JP2008150550A - Adhesive composition - Google Patents

Adhesive composition Download PDF

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JP2008150550A
JP2008150550A JP2006342636A JP2006342636A JP2008150550A JP 2008150550 A JP2008150550 A JP 2008150550A JP 2006342636 A JP2006342636 A JP 2006342636A JP 2006342636 A JP2006342636 A JP 2006342636A JP 2008150550 A JP2008150550 A JP 2008150550A
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adhesive composition
polystyrene
adhesive
monomer
composition according
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JP5116299B2 (en
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Masayuki Nishii
雅之 西井
Makoto Sakurai
櫻井　　良
Mitsuhiro Nishida
三博 西田
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Bridgestone Corp
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Bridgestone Corp
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Abstract

<P>PROBLEM TO BE SOLVED: To provide an adhesive composition exhibiting strong adhesive strength even when a substrate is bent, not only causing no adhesive peeling of the substrate and no sealing defects such as cracks and gaps at sealed parts but also dispensing with a massive apparatus for processing. <P>SOLUTION: The adhesive composition is obtained by containing a polymer exhibiting rubber elasticity and a monofunctional acrylic (or methacrylic) monomer as principal constituents and a thermal radical generator. Preferably, it is used for manufacturing a flexible information display panel composed of flexible substrates bonded together. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

本発明は、好ましくはフレキシブルディスプレイパネルの製造においてシール剤あるいは接着剤として利用することのできる接着剤組成物に関するものである。   The present invention preferably relates to an adhesive composition that can be used as a sealant or an adhesive in the manufacture of flexible display panels.

近年、薄型情報表示用パネルの技術が大きく進展し、我々の身の回りにテレビやノートパソコン、携帯電話のディスプレイパネルとして広く普及している。情報の表示方法は、液晶やプラズマ、ＥＬを用いた方法などが一般的であるが、近年、メモリー性を有する表示方法として新たに帯電粒子気中駆動方式や帯電粒子電気泳動方式などが開発されている。また、薄型情報表示用パネルの最近の大きな流れとして、折り曲げが可能で軽くて安全な(落としても割れない)フレキシブルタイプのディスプレイ、いわゆる電子ペーパーが注目されている。   In recent years, the technology of thin information display panels has greatly advanced, and it is widely used as display panels for TVs, notebook computers, and mobile phones. The information display method is generally a method using liquid crystal, plasma, EL, etc. Recently, a charged particle in-air drive method, a charged particle electrophoresis method, and the like have been newly developed as a display method having a memory property. ing. In addition, as a recent large flow of thin information display panels, a flexible display that can be bent and is light and safe (not broken when dropped), so-called electronic paper, has attracted attention.

一方、接着剤は、それら情報表示用パネルの製造において、基板の接着や表示部外周のシールによる水分のバリアといった重要な役割を果たしている。一般的に、ディスプレイパネル用シール剤、特に液晶ディスプレイの製造に用いるシール剤としては、熱硬化型の一液性エポキシ化合物が広く用いられている（例えば、特許文献１参照）。また、硬化時間短縮のためのアクリル系重合モノマーをベース高分子（エポキシアクリレートやウレタンアクリレート）に混合させ、光ラジカル発生剤により硬化させるシール剤が開発されている（例えば、特許文献２、特許文献３参照）。しかし、それらはいずれも剛直なガラス基板からなる情報表示用パネルに適用が限定され、フレキシブルな基板からなる情報表示用パネルに好適に用いられる接着剤（あるいはシール剤）は市販品には存在せず、特許文献も一部公開例があるのみで（特許文献４参照）、ほとんど例がなかった。
特開２０００−３４７２０３号公報 特開平７−１３１７５号公報 特許第３１６２１７９号公報 特公平６−９０３７９号公報 On the other hand, the adhesive plays an important role in the manufacture of such information display panels, such as adhesion of the substrate and moisture barrier by sealing the outer periphery of the display portion. Generally, a thermosetting one-component epoxy compound is widely used as a sealant for a display panel, particularly a sealant used for manufacturing a liquid crystal display (see, for example, Patent Document 1). Further, a sealing agent has been developed in which an acrylic polymerization monomer for shortening the curing time is mixed with a base polymer (epoxy acrylate or urethane acrylate) and cured with a photo radical generator (for example, Patent Document 2, Patent Document). 3). However, all of them are limited to information display panels made of rigid glass substrates, and there are no commercially available adhesives (or sealants) that are suitably used for information display panels made of flexible substrates. In addition, only a part of the patent document is disclosed (see Patent Document 4), and there are almost no examples.
JP 2000-347203 A Japanese Patent Laid-Open No. 7-13175 Japanese Patent No. 3162179 Japanese Patent Publication No. 6-90379

上述した従来技術のうち、特許文献１に示す例については、エポキシ材料は硬化反応に時間がかかるという問題があった。またそれらは、硬化物が硬い（過度の三次元架橋構造の形成）ため、パネル形状が変化しないガラス基板の接着には適しているが、折り曲げといった形状変化が起こるフィルムパネルからなるフレキシブルディスプレイ用のシール剤（あるいは接着剤）としては、曲げの形状変化に対して接着力が弱く、剥がれに対しても弱いといった問題があった。また、特許文献２あるいは特許文献３に示す例については、大掛かりな紫外光照射設備の設置が必要などの制約が生じる問題があった。   Among the above-described prior arts, the example shown in Patent Document 1 has a problem that the epoxy material takes time for the curing reaction. They are hardened (formation of an excessive three-dimensional cross-linked structure) and are suitable for bonding to a glass substrate where the panel shape does not change, but for flexible displays made of film panels that undergo shape changes such as bending. As a sealing agent (or adhesive), there is a problem that the adhesive force is weak with respect to a bending shape change, and it is also weak against peeling. In addition, the example shown in Patent Document 2 or Patent Document 3 has a problem in that there is a restriction that it is necessary to install a large-scale ultraviolet light irradiation facility.

本発明の目的は、上述した問題点を解消して、基板を曲げた場合でも強い接着力を示し、基板の剥がれや、シールした部分に隙間や亀裂等のシール性不具合を発生させないばかりではなく、その施工に大掛かりな設備を必要としない接着剤組成物を提供しようとするものである。   The object of the present invention is not only to solve the above-mentioned problems, but to show a strong adhesive force even when the substrate is bent, and not only cause the substrate to peel off, but also cause a sealing failure such as a gap or a crack in the sealed portion. The present invention intends to provide an adhesive composition that does not require large-scale equipment for its construction.

本発明の接着剤組成物は、ゴム弾性を示す高分子および単官能アクリル（またはメタクリル）系モノマーを主成分とし、熱ラジカル発生剤を含有してなることを特徴とするものである。   The adhesive composition of the present invention is characterized by comprising a polymer exhibiting rubber elasticity and a monofunctional acrylic (or methacrylic) monomer as a main component and a thermal radical generator.

本発明の接着剤組成物の好適例としては、ゴム弾性を示す高分子１００重量部に対し、モノマーが２０〜１８０重量部であること、ゴム弾性を示す高分子が、ブチルゴム、ハロゲン化ブチルゴム、ブタジエンゴム、ＳＢＳ（ポリスチレン＝ポリブタジエン＝ポリスチレン）、ＳＩＳ（ポリスチレン＝ポリイソプレン＝ポリスチレン）、ＳＥＢＳ（ポリスチレン＝ポリ（エチレン＝ブチレン）＝ポリスチレン）などのエラストマーであること、架橋剤を含有すること、シランカップリング剤を含有すること、可とう性を要する部分に適用されること、フレキシブルな基板を貼り合わせて構成するフレキシブルな情報表示用パネルに用いることができること、少なくとも一方が透明な対向する２枚のフレキシブルな基板間の空間に、少なくとも１種類以上の粒子から構成される光学的反射率および帯電性を有する表示媒体を少なくとも１種類以上封入し、表示媒体に電界を付与することによって、表示媒体を移動させて画像等の情報を表示する情報表示用パネルの製造に用いること、がある。   As a preferable example of the adhesive composition of the present invention, the monomer is 20 to 180 parts by weight with respect to 100 parts by weight of the polymer exhibiting rubber elasticity, and the polymer exhibiting rubber elasticity is butyl rubber, halogenated butyl rubber, It is an elastomer such as butadiene rubber, SBS (polystyrene = polybutadiene = polystyrene), SIS (polystyrene = polyisoprene = polystyrene), SEBS (polystyrene = poly (ethylene = butylene) = polystyrene), contains a crosslinking agent, silane It contains a coupling agent, is applied to a portion that requires flexibility, can be used for a flexible information display panel formed by bonding a flexible substrate, and at least one of two facing transparent sheets At least 1 in the space between the flexible substrates At least one type of display medium having optical reflectivity and chargeability composed of particles of at least one kind is encapsulated, and an electric field is applied to the display medium, whereby the display medium is moved to display information such as an image. It may be used for manufacturing information display panels.

本発明では、ゴム弾性を示す高分子および単官能アクリル（またはメタクリル）系モノマーを主成分とし、熱ラジカル発生剤を含有してなる組成とすることで、フレキシブルな基板を曲げた場合でも強い接着力を示し、基板の接着剥がれや、シールした部分に隙間や亀裂等のシール性不具合を発生させないばかりではなく、その施工に大掛かりな設備を必要としない接着剤組成物を得ることができる。   In the present invention, a composition comprising a polymer having rubber elasticity and a monofunctional acrylic (or methacrylic) monomer as a main component and a thermal radical generator is included, so that even when a flexible substrate is bent, strong adhesion is achieved. It is possible to obtain an adhesive composition that exhibits strength and does not cause adhesion peeling of the substrate or occurrence of sealing problems such as gaps and cracks in the sealed portion, and does not require extensive equipment for its construction.

本発明の接着剤配合物は、各種情報表示用パネルの基板の接着、特に、フレキシブルな情報表示用パネルの基板の接着や表示部外周のシールに適している。被着部分としては、図１に示すようなフレキシブルなフィルム同士の接着はもちろん、可とう性を要する部分、例えばフレキシブルなフィルムとリジッドな隔壁の接着にも好適に用いることができる。   The adhesive composition of the present invention is suitable for bonding substrates of various information display panels, in particular, bonding of flexible information display panel substrates and sealing of the outer periphery of the display section. As an adherent portion, it can be suitably used not only for bonding flexible films as shown in FIG. 1 but also for a portion requiring flexibility, for example, bonding of a flexible film and a rigid partition wall.

情報表示用パネルの例として、帯電粒子駆動型フレキシブルディスプレイパネルを示す（図２）。少なくとも１種類以上の粒子から構成される光学的反射率および帯電特性の異なる少なくとも２種以上の表示媒体３（ここでは白色表示媒体用粒子３Ｗａの粒子群からなる白色表示媒体３Ｗと黒色表示媒体用粒子３Ｂａの粒子群からなる黒色表示媒体３Ｂを示す）を、隔壁４で形成された各セルにおいて、フレキシブル基板１に設けた電極５（ライン電極）とフレキシブル基板２に設けた電極６（ライン電極）との間に電圧を印加することにより発生する電界に応じて、基板１、２と垂直に移動させる。そして、図２（ａ）に示すように白色表示媒体３Ｗを観察者に視認させて白色の表示を行なうか、あるいは、図２（ｂ）に示すように黒色表示媒体３Ｂを観察者に視認させて黒色の表示を行なっている。なお、図２（ａ）、（ｂ）において、手前にある隔壁は省略している。また、表示媒体としては、上述した帯電粒子のほか帯電粒子を絶縁性液体とともにマイクロカプセルに封入したものや、液晶など様々な表示媒体が挙げられるが、本発明の接着剤組成物はいずれの表示媒体を用いた情報表示用パネルにも適用できる。   As an example of the information display panel, a charged particle driven flexible display panel is shown (FIG. 2). At least two or more kinds of display media 3 (here, white display medium 3W composed of particles of white display medium particles 3Wa and black display medium) which are composed of at least one kind of particles and have different optical reflectance and charging characteristics. In each cell formed with the partition walls 4, an electrode 5 (line electrode) provided on the flexible substrate 1 and an electrode 6 (line electrode) provided on the flexible substrate 2 are used to display a black display medium 3 </ b> B composed of particles of particles 3Ba. ) Between the substrates 1 and 2 according to the electric field generated by applying a voltage between them. Then, the white display medium 3W is visually recognized by the observer as shown in FIG. 2A, or white display is performed, or the black display medium 3B is visually recognized by the observer as shown in FIG. 2B. Are displayed in black. In addition, in FIG. 2 (a), (b), the partition in front is abbreviate | omitted. Examples of the display medium include various display media such as a liquid crystal in which charged particles are enclosed in a microcapsule together with an insulating liquid in addition to the above-described charged particles, and the adhesive composition of the present invention may be any display. The present invention can also be applied to an information display panel using a medium.

本発明の特徴は、組成をゴム弾性を示す高分子および単官能アクリル（またはメタクリル）系モノマーを主成分とし、熱ラジカル発生剤を含有してなる組成とした接着剤組成物にあり、本発明の接着剤組成物は、特に、種々の構成の情報表示用パネルの製造において、図１に示すように、フレキシブルな上下基板同士の接着、フレキシブルな基板とリジッドな隔壁との接着、および情報表示部の周囲のシール、などに好適に用いることができる。   A feature of the present invention resides in an adhesive composition having a composition comprising a polymer having rubber elasticity and a monofunctional acrylic (or methacrylic) monomer as a main component and a thermal radical generator. In particular, in the production of information display panels having various configurations, as shown in FIG. 1, the adhesive composition of FIG. 1 is bonded between flexible upper and lower substrates, bonded between a flexible substrate and a rigid partition, and information display. It can be suitably used for a seal around the part.

本発明の接着剤組成物は、重合モノマーとして単官能のアクリル（またはメタクリル）系モノマーを用いることにより、エポキシ系の接着剤に比べて硬化物の架橋密度を低減させている。また、ゴム弾性を示す高分子をベースポリマーとすることにより、接着後の基板の曲げやはがれの変形に対して強い接着力を示す配合物としている。さらに、熱ラジカル反応によるオレフィンの重合反応を適用し、エポキシ材料に比べて硬化時間を短縮、かつ貯蔵安定性を向上させている。   The adhesive composition of the present invention uses a monofunctional acrylic (or methacrylic) monomer as a polymerization monomer, thereby reducing the crosslink density of the cured product as compared with an epoxy adhesive. In addition, by using a polymer exhibiting rubber elasticity as a base polymer, a compound exhibiting strong adhesive strength against bending and peeling deformation of the substrate after bonding is obtained. Furthermore, by applying a polymerization reaction of olefin by thermal radical reaction, the curing time is shortened and the storage stability is improved as compared with the epoxy material.

本発明の接着剤組成物において、ベースポリマーであるゴム弾性を示す高分子としては、天然ゴムや合成ゴム、例えばブチルゴム、ハロゲン化ブチルゴム、ブタジエンゴム、ＳＢＳ、ＳＩＳ、ＳＥＢＳなどが適用できる。分子量は１０００程度のオリゴマーから１００万以上のポリマーまで広く適用できる。モノマーとしては、各種アクリル酸またはメタクリル酸エステルが用いられ、置換基としては、メチル基、エチル基、ブチル基、ヘキシル基、オクチル基、デシル基、ウンデシル基、テトラデシル基、オクタデシル基などの直鎖アルキル基や、イソブチル基やイソプロピル基など分岐構造を有するもの、さらに、シクロヘキシル基などの脂環式の誘導体が適用できる。ベンジル基や２−ヒドロキシエチル基で置換されたアクリレート（またはメタクリレート）などは、単独で上述のベースポリマーと混合すると相溶せず、取り扱いが困難になる。組成は、ベースポリマー１００重量部に対し、モノマーが２０〜１８０重量部であることが望ましい。２官能あるいは多官能モノマーは単独では上述のベースポリマーと相溶しないが、ベースポリマーと相溶する単官能モノマーに対する架橋剤として用いることができ、２官能モノマーであれば単官能モノマーに対して７０重量％まで、多官能モノマーであれば単官能モノマーに対して５重量％程度まで用いることができる。架橋剤としては、２官能以上のメタクリル（あるいはアクリル）化合物、例えばトリメチロールプロパントリアクリレートやアルキルジオールメタクリレート、などが適用できる。   In the adhesive composition of the present invention, natural rubber or synthetic rubber such as butyl rubber, halogenated butyl rubber, butadiene rubber, SBS, SIS, SEBS, etc. can be applied as the base polymer having rubber elasticity. The molecular weight can be widely applied from oligomers of about 1000 to polymers of 1 million or more. As the monomer, various acrylic acid or methacrylic acid esters are used, and as the substituent, linear groups such as methyl group, ethyl group, butyl group, hexyl group, octyl group, decyl group, undecyl group, tetradecyl group, octadecyl group, etc. An alkyl group, one having a branched structure such as an isobutyl group or isopropyl group, and an alicyclic derivative such as a cyclohexyl group can be applied. An acrylate (or methacrylate) substituted with a benzyl group or a 2-hydroxyethyl group is not compatible with the above-mentioned base polymer alone and is difficult to handle. As for composition, it is desirable that a monomer is 20-180 weight part with respect to 100 weight part of base polymers. A bifunctional or polyfunctional monomer alone is not compatible with the above-mentioned base polymer, but can be used as a crosslinking agent for a monofunctional monomer compatible with the base polymer. If it is a polyfunctional monomer up to 5% by weight, it can be used up to about 5% by weight relative to the monofunctional monomer. As the crosslinking agent, a bifunctional or higher methacrylic (or acrylic) compound such as trimethylolpropane triacrylate or alkyldiol methacrylate can be used.

本発明の接着剤組成物では、主成分となるベースポリマーおよびモノマーに対して、熱ラジカル発生剤（重合開始剤）を添加し、必要に応じてシランカップリング剤を添加する。   In the adhesive composition of the present invention, a thermal radical generator (polymerization initiator) is added to the base polymer and monomer as main components, and a silane coupling agent is added as necessary.

ここで、熱ラジカル発生剤（重合開始剤）としては、熱開裂性のパーオキサイド、例えば、ベンゾイルパーオキサイド、ｔ−ブチルパーオキシイソプロピルモノカーボネートなどが適用できるが、貯蔵安定性や加工条件を考慮すると、１時間半減期温度が７０〜１００℃のものが望ましい。シランカップリング剤としては、３−メタクロキシプロピルトリメトキシシラン、３−メタクロキシプロピルトリエトキシシラン、３−アミノプロピルトリメトキシシラン、３−アミノプロピルトリエトキシシラン、などが適用できる。   Here, as the thermal radical generator (polymerization initiator), thermo-cleavable peroxides such as benzoyl peroxide and t-butyl peroxyisopropyl monocarbonate can be applied, but storage stability and processing conditions are taken into consideration. Then, a one-hour half-life temperature of 70-100 degreeC is desirable. As the silane coupling agent, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, and the like can be applied.

本発明の接着剤組成物は、塗布方法によって適宜、有機溶剤を混合して粘度を調整できる。例えば、印刷機で塗布する場合は無溶剤で用いられるが、ディスペンサーで塗布する場合は溶剤で低粘度化する必要がある。溶剤としては、酢酸エチル、エタノール、トルエンなど汎用の有機溶剤が適用できる。   The adhesive composition of the present invention can be adjusted in viscosity by appropriately mixing an organic solvent depending on the coating method. For example, when applying with a printing machine, it is used without a solvent, but when applying with a dispenser, it is necessary to lower the viscosity with a solvent. As the solvent, general-purpose organic solvents such as ethyl acetate, ethanol and toluene can be applied.

以下、実際の例について説明する。 Hereinafter, an actual example will be described.

＜接着剤組成物の作製＞
ゴム弾性を示す高分子として、以下の化１に示す構造のブチルゴム １（平均分子量５０万）、ブロモ化ブチルゴム ２(平均分子量５０万)、およびＳＥＢＳ ３（平均分子量１１万）を準備し、モノマーとして、化２に示す構造の2−エチルヘキシルメタクリレート ４、ドデシルメタクリレート ５、ベンジルメタクリレート ６、グリシジルメタクリレート ７、２−ヒドロキシ−３−フェノキシプロピルアクリレート ８、２−メタクリロイルオキシエチルアシッドフォスフェート ９、および２−メタクリロイルオキシエチルフタル酸 １０ を準備し、さらに架橋剤として以下の化３に示す構造の１，９−ノナンジオールジアクリレート １１ およびトリメチロールプロパントリアクリレート １２ を、熱ラジカル発生剤（重合開始剤）として、以下の化４に示すベンゾイルパーオキサイド １３（１時間半減期温度が９０度）を、シランカップリング剤として３−メタクロキシプロピルトリメトキシシラン １４ を準備した。これらを以下の表１〜表３に示す配合比で混合して配合物Ｎｏ．１−１〜Ｎｏ．３−１０の配合物を得た。また比較例として、室温でゴム弾性を示さない高分子であるポリメタクリル酸メチル １５ および、市販品の一液性エポキシ接着剤（エポキシオリゴマーと潜在性硬化剤からなる液晶ディスプレイ用のシール剤）を準備した。配合および結果を表１に示す。 <Preparation of adhesive composition>
As polymers exhibiting rubber elasticity, butyl rubber 1 (average molecular weight 500,000), brominated butyl rubber 2 (average molecular weight 500,000), and SEBS 3 (average molecular weight 110,000) having the structure shown in the following chemical formula 1 are prepared, and monomers 2-ethylhexyl methacrylate 4, dodecyl methacrylate 5, benzyl methacrylate 6, glycidyl methacrylate 7, 2-hydroxy-3-phenoxypropyl acrylate 8, 2-methacryloyloxyethyl acid phosphate 9, and 2- Methacryloyloxyethylphthalic acid 10 is prepared, and 1,9-nonanediol diacrylate 11 and trimethylolpropane triacrylate 12 having the structure shown in the following chemical formula 3 are used as a crosslinking agent as a thermal radical generator (polymerization initiator). , Benzoyl peroxide 13 shown in Chemical formula 4 (1 hour half-life temperature 90 °) was prepared 3-methacryloyloxy trimethoxysilane 14 as the silane coupling agent. These were mixed by the compounding ratio shown in the following Tables 1 to 3, and the compound No. 1-1-No. A formulation of 3-10 was obtained. As a comparative example, polymethyl methacrylate 15 which is a polymer that does not exhibit rubber elasticity at room temperature and a commercially available one-part epoxy adhesive (a sealing agent for liquid crystal displays comprising an epoxy oligomer and a latent curing agent) Got ready. The formulation and results are shown in Table 1.

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＜接着剤組成物の評価＞
作製した配合物の性能評価に関しては、プラスチック基材に対する接着力、配合物の水分バリア性、弾性率、およびフレキシブルパネル作製時の強度について調べた。 <Evaluation of adhesive composition>
Regarding the performance evaluation of the prepared blend, the adhesive strength to the plastic substrate, the moisture barrier property of the blend, the elastic modulus, and the strength at the time of preparing the flexible panel were examined.

接着力は、フィルム基材に対する１８０°ピール試験により評価した。ピール試験の模式図を図３に示す。試験片は、厚さ１２５mｍのフィルム上に配合物を塗布した後、ギャップを４０mｍに保ちながら対向フィルムと加熱・圧着（１００℃，１時間）して作製した。貼り合わせたフィルムを幅１ｃｍに裁断して、オートグラフによりフィルムの上下端を５ｃｍ／ｍｉｎの速度で引っ張り、応力の平均値を接着力とした。フィルム基板は、polyethylene terephthalate (PET), polyethylene sulfate (PES), polycarbonate (PC)など種々のプラスチックフィルムが適用できる。ＰＥＴフィルムでの結果を表１〜表３に示す。   The adhesive strength was evaluated by a 180 ° peel test on the film substrate. A schematic diagram of the peel test is shown in FIG. The test piece was prepared by applying the composition on a film having a thickness of 125 mm and then heating and pressing (100 ° C., 1 hour) with the counter film while keeping the gap at 40 mm. The bonded film was cut into a width of 1 cm, and the upper and lower ends of the film were pulled at a rate of 5 cm / min by an autograph, and the average value of the stress was defined as the adhesive strength. Various plastic films such as polyethylene terephthalate (PET), polyethylene sulfate (PES), and coating (PC) can be applied to the film substrate. The results with PET films are shown in Tables 1 to 3.

水分バリア性は配合物をキャスト法により製膜（厚さ １００ μｍ 程度）、 加熱・硬化後（１００℃、１時間）、ＭＯＣＯＮ法（条件:４０℃、９０％）により測定した。   The moisture barrier property was measured by the MOCON method (conditions: 40 ° C., 90%) after film formation of the compound by a casting method (thickness of about 100 μm), after heating and curing (100 ° C., 1 hour).

弾性率については、レオメーターにより調べた。   The elastic modulus was examined with a rheometer.

配合物のフレキシブルディスプレイ用シール剤および接着剤としての適合性は、図５に示すような繰り返し折り曲げ試験で評価した。図４（ａ）ではシール剤を想定し、厚さ１２５mｍのＰＥＴフィルム基板に試料を図のように塗布して、もう一枚のフィルム基板と重ね合わせて接着させて空パネルとした（スペーサーを用いて、フィルム基板間ギャップを４０mｍとした）。作製した重ね合わせパネルを折り曲げ試験機にかけ試験を行い、フィルム基板と接着剤がはがれるまでの折り曲げ試験回数を調べた。また、図５（ｂ）に示す構成の表示媒体未充填の隔壁付空パネルで、剛直な壁隔（厚さ４０μｍ）とフレキシブルな基板との接着力を同様な折り曲げ試験により調べた。   The compatibility of the blend as a sealant and adhesive for flexible displays was evaluated by a repeated bending test as shown in FIG. In FIG. 4 (a), assuming a sealing agent, a sample is applied to a PET film substrate having a thickness of 125 mm as shown in FIG. And the gap between the film substrates was 40 mm). The produced overlapping panel was subjected to a bending tester and tested, and the number of bending tests until the film substrate and the adhesive were peeled was examined. Further, the adhesive force between the rigid wall space (thickness: 40 μm) and the flexible substrate was examined by a similar bending test in the empty panel with a partition wall that was not filled with the display medium having the configuration shown in FIG.

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表１の結果から、ブチルゴム系、ＳＥＢＳ系ともに、単官能モノマー 4 を混合することにより接着力が大きく増大することがわかった。ブチルゴム 1 単独（表１； 配合物Ｎｏ．１−１）では、７０Ｎ／ｍの接着力しか示さなかったのに対し、モノマー 4 を混合するにつれて接着力が増大し、１．４倍重量混合した配合物（表１；配合物Ｎｏ．１−５）では、３７０Ｎ／ｍと５倍以上の接着力が得られた。ＳＥＢＳ系においても、単独での接着力（１５０Ｎ／ｍ、配合物Ｎｏ．１−７）がモノマーを混合することにより大きく増大した（〜４１０Ｎ．ｍ、配合物Ｎｏ．１−８〜Ｎｏ．１−１１）。これに対して、この試験環境（室温）においてゴム弾性を示さないpolymethyl methacrylate (ＰＭＭＡ) 15（比較例）は、単独の接着力も非常に弱くさらに、モノマーを混合してもフィルム基板に対する接着力の向上はほとんど観察されなかった（配合物Ｎｏ．１−１３およびＮｏ．１−１４）。さらに市販のエポキシ系接着剤（液晶ディスプレイ用のシール剤）も、フィルム基板へのピール接着力は非常に弱いことがわかった（表１）。これより、フィルム基板の接着に対しては、ゴム性高分子の弾性やアクリル系重合物の粘着性が重要な役割を果たしていることが示唆された。特に硬化物の弾性率が重要であると考えられ、固体高分子であるＰＭＭＡや市販のエポキシ型接着剤は室温での弾性率がそれぞれ１０の９乗のオーダーと、とても硬い材料であるのに対して（表１）、本発明の接着剤組成物は硬化後の室温での弾性率が１０の５乗オーダーと非常に柔らかい材料であり、この特性によりフィルムのはがれ時に発生する応力を分散・吸収していると考えられる（表１）。   From the results shown in Table 1, it was found that the adhesive strength was greatly increased by mixing the monofunctional monomer 4 in both the butyl rubber system and the SEBS system. Butyl rubber 1 alone (Table 1; Formulation No. 1-1) showed only an adhesive strength of 70 N / m, whereas as the monomer 4 was mixed, the adhesive strength increased and 1.4 times the weight was mixed. In the blends (Table 1; blend No. 1-5), 370 N / m and an adhesive force of 5 times or more were obtained. Also in the SEBS system, the adhesive strength by itself (150 N / m, formulation No. 1-7) was greatly increased by mixing the monomers (˜410 N.m, formulation No. 1-8 to No. 1). -11). In contrast, polymethyl methacrylate (PMMA) 15 (comparative example), which does not exhibit rubber elasticity in this test environment (room temperature), has a very weak single adhesive force, and even when a monomer is mixed, the adhesive strength to the film substrate is low. Little improvement was observed (Formulations No. 1-13 and No. 1-14). Furthermore, it was found that a commercially available epoxy adhesive (sealant for liquid crystal display) also had very weak peel adhesion to the film substrate (Table 1). This suggests that the elasticity of the rubbery polymer and the tackiness of the acrylic polymer play an important role in the adhesion of the film substrate. In particular, the elastic modulus of the cured product is considered to be important, and PMMA, which is a solid polymer, and commercially available epoxy adhesives are very hard materials, each having an elastic modulus on the order of 10 to the 9th power at room temperature. On the other hand (Table 1), the adhesive composition of the present invention is an extremely soft material having a modulus of elasticity at room temperature after curing, on the order of 10 5, and this characteristic disperses the stress generated when the film peels. It is thought that it absorbs (Table 1).

ベースポリマーに対するモノマーの配合量は増やしすぎると接着力に不利に働いた（配合物Ｎｏ．１−６、Ｎｏ．１−１２）。モノマーの添加量はベースポリマー１００重量部に対して２０〜１８０重量部が適している。   When the compounding quantity of the monomer with respect to the base polymer was increased too much, it adversely affected the adhesive force (formulation No. 1-6, No. 1-12). The amount of monomer added is suitably 20 to 180 parts by weight per 100 parts by weight of the base polymer.

水分バリア性に関しては、ベースポリマー単独で得られたバリア性がモノマーの混合・硬化後も維持された（表１）。特にブチルゴム系では、８〜９ｇ／ｍ２・ｄａｙと市販の液晶ディスプレイ用のシール剤であるエポキシ系接着剤（１３ｇ／ｍ２・ｄａｙ）よりも優れた性能が見られた。本発明は、有機系の接着剤配合物としては非常に高いバリア性を有する材料であり、ディスプレイ用シール剤として非常に有用である。 Regarding the moisture barrier property, the barrier property obtained with the base polymer alone was maintained even after mixing and curing of the monomers (Table 1). In particular butyl rubber, 8~9g / m 2 · day and a commercially available epoxy adhesive is a sealant for a liquid crystal display (13g / m 2 · day) superior performance was observed. The present invention is a material having a very high barrier property as an organic adhesive compound, and is very useful as a sealant for a display.

表２にベースポリマー 2 に対して各種単官能モノマーを混合した結果を示す。表１で最も良好な接着力が得られた配合比（ベースポリマー：単官能モノマー＝１００：１４０）でそれぞれ混合したところ、脂肪族アルキル基で置換されたモノマーである 4 や 5 はベースポリマー 2 と相溶して適度な接着力を示したのに対し（配合物Ｎｏ．２−１、Ｎｏ．２−２）、モノマー間の凝集力のより強いベンゼン環の誘導体 6 や分子中に極性部位を有する 7, 8, 9, 10 は、ベースポリマーと均一に相溶しなかった。しかし、表２中配合物Ｎｏ．２−８〜Ｎｏ．２−１２で示すように、モノマーを二成分系としてベースポリマーにより相溶しやすいモノマー（ここでは 4）に 7 〜 10 を少量添加した場合、均一な混合物が得られた。とくに、極性のより高いリン酸基やカルボキシル基を有するモノマーの場合、接着力に対して有利に働くことがわかった（Ｎｏ．２−１１、Ｎｏ．２−１２）。さらに、単官能モノマーを３成分以上にした場合も同様な傾向が見られた。   Table 2 shows the results of mixing various monofunctional monomers with the base polymer 2. When mixed at the blending ratio (base polymer: monofunctional monomer = 100: 140) at which the best adhesive strength was obtained in Table 1, monomers 4 and 5 substituted with aliphatic alkyl groups were base polymer 2 The benzene ring derivative 6 with stronger cohesion between monomers and polar sites in the molecule, while having a suitable adhesive strength (composition No. 2-1, No. 2-2) 7, 8, 9 and 10 having a ratio were not uniformly compatible with the base polymer. However, in Table 2, the formulation No. 2-8-No. As shown in 2-12, when a small amount of 7 to 10 was added to a monomer (here, 4) that is compatible with the base polymer using the monomer as a two-component system, a uniform mixture was obtained. In particular, in the case of a monomer having a higher polarity phosphate group or carboxyl group, it was found that it works favorably with respect to adhesive strength (No. 2-11, No. 2-12). Furthermore, the same tendency was observed when the monofunctional monomer was composed of three or more components.

接着剤配合物に対する架橋剤の効果を表３に示す。２官能性の 11 と３官能性の 12 に関して、単独ではそれぞれベースポリマーと相溶しないが、単官能モノマー 4 に添加していく場合、２官能性架橋剤 11 はベースポリマーと等量まで、３官能性架橋剤 12 は５重量部まで相溶した。特に２官能架橋剤を添加した配合物Ｎｏ．３−１〜Ｎｏ．３−４では、接着力の顕著な向上が観察された。これに対し３官能架橋剤では、微量の添加なら効果は見られたが（配合物Ｎｏ．３−７）、３重量部以上添加すると接着力が大きく低下した（配合物Ｎｏ．３−８、Ｎｏ．３−９）。また弾性率に関しては、架橋剤を混合させることで１０倍程度増加したが、それでも固体高分子（配合物Ｎｏ．１−１３や液晶ディスプレイ用シール剤）と比較するとまだ十分に柔らかい。   The effect of the crosslinking agent on the adhesive formulation is shown in Table 3. Regarding bifunctional 11 and trifunctional 12 alone, they are not compatible with the base polymer alone, but when added to the monofunctional monomer 4, the bifunctional crosslinker 11 is up to the same amount as the base polymer. The functional crosslinking agent 12 was compatible up to 5 parts by weight. In particular, Formulation No. 2 to which a bifunctional crosslinking agent was added. 3-1. In 3-4, the remarkable improvement of the adhesive force was observed. On the other hand, in the case of the trifunctional cross-linking agent, an effect was seen if it was added in a small amount (Compound No. 3-7), but when it was added in an amount of 3 parts by weight or more, the adhesive strength was greatly reduced (Compound No. 3-8, No. 3-9). Further, the elastic modulus increased about 10 times by mixing the cross-linking agent, but it is still sufficiently soft as compared with the solid polymer (formulation No. 1-13 and the sealing agent for liquid crystal display).

配合物の硬化挙動は弾性率測定により確認した。配合物Ｎｏ．３−７の測定結果を図４に示す。１００℃到達後１０分が経過したあたりから弾性率の増加が観察され、４０分程度で重合がほぼ完了することがわかった。また、配合物Ｎｏ．３−７の接着力の促進試験（信頼性評価）結果を表４に示す。測定は、温度６０℃、湿度９０％の恒温槽に所定時間投入後、温度２５℃、湿度５０％の環境に１日静置した後に行った。結果、配合物Ｎｏ．３−７は１０００時間後も初期の接着力を維持しており、高い信頼性を有していることがわかった。   The cure behavior of the formulation was confirmed by elastic modulus measurement. Formulation no. The measurement results of 3-7 are shown in FIG. An increase in elastic modulus was observed around 10 minutes after reaching 100 ° C., and it was found that the polymerization was almost completed in about 40 minutes. Also, the formulation No. Table 4 shows the results of 3-7 adhesion force acceleration test (reliability evaluation). The measurement was carried out after being placed in a thermostat having a temperature of 60 ° C. and a humidity of 90% for a predetermined time, and then allowed to stand in an environment of a temperature of 25 ° C. and a humidity of 50% for one day. Results, formulation no. 3-7 maintained the initial adhesive force even after 1000 hours, and was found to have high reliability.

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本発明のフレキシブルディスプレイ用シール剤（あるいは接着剤）への適用性を調べるため、図５に示すような繰り返し折り曲げ試験を行った。図５（ａ）の系では、液晶ディスプレイ用シール剤として市販されているエポキシ系接着剤が、５０回程度の折り曲げで上下のフィルムがはがれてしまったのに対し、本発明の接着剤組成物、例えば配合物Ｎｏ．３−７では、５万回以上の折り曲げに対しても全くはがれることなく初期の接着形態が維持された。図５（ｂ）の系においても、本発明の接着剤組成物は数万回以上の折り曲げ耐久性を示した。   In order to examine the applicability to the sealing agent (or adhesive) for flexible displays of the present invention, a repeated bending test as shown in FIG. 5 was performed. In the system shown in FIG. 5 (a), the epoxy adhesive marketed as a sealant for liquid crystal displays has peeled off the upper and lower films after being bent about 50 times, whereas the adhesive composition of the present invention. For example, formulation no. In 3-7, the initial adhesive form was maintained without being peeled at all even after bending of 50,000 times or more. Even in the system of FIG. 5 (b), the adhesive composition of the present invention exhibited a bending durability of tens of thousands of times.

本発明の接着剤組成物は、フレキシブルな板材を貼り合わせて構成されるフレキシブルディスプレイパネルのようなパネル型製品や、フレキシブルな板材上にリジッドな物を貼り付けて構成される製品に対して好適に用いられる。   The adhesive composition of the present invention is suitable for panel type products such as flexible display panels configured by bonding flexible plate materials, and products configured by bonding rigid objects on flexible plate materials. Used for.

本発明の接着剤組成物の情報表示用パネル内での適用部の一例を示す図である。It is a figure which shows an example of the application part in the information display panel of the adhesive composition of this invention. （ａ）、（ｂ）はそれぞれ本発明の接着剤組成物を用いた情報表示用パネルの一例を示す図である。(A), (b) is a figure which shows an example of the panel for information displays using the adhesive composition of this invention, respectively. ピール試験を説明するための模式図である。It is a schematic diagram for demonstrating a peel test. 実施例における配合物Ｎｏ．３−７の硬化挙動を示すグラフである。Formulation No. in Examples It is a graph which shows the hardening behavior of 3-7. （ａ）、（ｂ）はそれぞれ実施例における繰り返し折り曲げ試験を説明するための模式図である。(A), (b) is a schematic diagram for demonstrating the repeated bending test in an Example, respectively.

符号の説明Explanation of symbols

１、２ フレキシブル基板
３ 表示媒体
３Ｗ 白色表示媒体
３Ｗａ 表示用白色粒子
３Ｂ 黒色表示媒体
３Ｂａ 表示用黒色粒子
４ 隔壁
５、６ 電極
1, 2 Flexible substrate 3 Display medium 3W White display medium 3Wa White particles for display 3B Black display medium 3Ba Black particles for display 4 Bulkhead 5, 6 Electrode

Claims (8)

ゴム弾性を示す高分子および単官能アクリル系 (あるいはメタクリル系) モノマーを主成分とし、熱ラジカル発生剤を含有してなることを特徴とする接着剤組成物。 An adhesive composition comprising a polymer having rubber elasticity and a monofunctional acrylic (or methacrylic) monomer as a main component and a thermal radical generator. ゴム弾性を示す高分子１００重量部に対し、モノマーが２０〜１８０重量部であることを特徴とする請求項１に記載の接着剤組成物。 The adhesive composition according to claim 1, wherein the monomer is 20 to 180 parts by weight with respect to 100 parts by weight of the polymer exhibiting rubber elasticity. ゴム弾性を示す高分子が、ブチルゴム、ハロゲン化ブチルゴム、ブタジエンゴム、ＳＢＳ（ポリスチレン＝ポリブタジエン＝ポリスチレン）、ＳＩＳ（ポリスチレン＝ポリイソプレン＝ポリスチレン）、ＳＥＢＳ（ポリスチレン＝ポリ（エチレン＝ブチレン）＝ポリスチレン）などの合成ゴムであることを特徴とする請求項１または２の接着剤組成物。 Polymers exhibiting rubber elasticity are butyl rubber, halogenated butyl rubber, butadiene rubber, SBS (polystyrene = polybutadiene = polystyrene), SIS (polystyrene = polyisoprene = polystyrene), SEBS (polystyrene = poly (ethylene = butylene) = polystyrene), etc. The adhesive composition according to claim 1, wherein the adhesive composition is a synthetic rubber. 架橋剤を含有することを特徴とする請求項１〜３のいずれか１項に記載の接着剤組成物。   The adhesive composition according to any one of claims 1 to 3, further comprising a crosslinking agent. シランカップリング剤を含有することを特徴とする請求項１〜４のいずれか１項に記載の接着剤組成物。   A silane coupling agent is contained, The adhesive composition of any one of Claims 1-4 characterized by the above-mentioned. 可とう性を要する部分に適用することを特徴とする請求項１〜５のいずれか１項に記載の接着剤組成物。   The adhesive composition according to claim 1, wherein the adhesive composition is applied to a portion requiring flexibility. フレキシブルな基板を貼り合わせて構成するフレキシブルな情報表示用パネルに用いることのできることを特徴とする請求項１〜６のいずれか１項に記載の接着剤組成物。   The adhesive composition according to any one of claims 1 to 6, wherein the adhesive composition can be used for a flexible information display panel formed by bonding a flexible substrate. 少なくとも一方が透明な対向する２枚のフレキシブルな基板間の空間に、少なくとも１種類以上の粒子から構成される光学的反射率および帯電性を有する表示媒体を少なくとも１種類以上封入し、表示媒体に電界を付与することによって、表示媒体を移動させて画像等の情報を表示する情報表示用パネルの製造に用いることを特徴とする請求項１〜７のいずれか１項に記載の接着剤組成物。   At least one or more display media having optical reflectivity and chargeability composed of at least one kind of particles are sealed in a space between two opposing flexible substrates, at least one of which is transparent. The adhesive composition according to any one of claims 1 to 7, wherein the adhesive composition is used for manufacturing an information display panel that displays information such as an image by moving a display medium by applying an electric field. .
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