JPH0798926B2 - Acrylic adhesive composition - Google Patents
Acrylic adhesive compositionInfo
- Publication number
- JPH0798926B2 JPH0798926B2 JP63152591A JP15259188A JPH0798926B2 JP H0798926 B2 JPH0798926 B2 JP H0798926B2 JP 63152591 A JP63152591 A JP 63152591A JP 15259188 A JP15259188 A JP 15259188A JP H0798926 B2 JPH0798926 B2 JP H0798926B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- sensitive adhesive
- acrylic
- acrylic acid
- 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.)
- Expired - Fee Related
Links
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、粘着力、凝集力並びに耐熱性に優れ、被着体
や支持体の加水分解を阻止しうるアクリル系粘着剤組成
物に関する。TECHNICAL FIELD The present invention relates to an acrylic pressure-sensitive adhesive composition that has excellent adhesive strength, cohesive strength, and heat resistance and can prevent hydrolysis of an adherend or a support.
（従来の技術） アクリル系粘着剤の一般的な組成は、15重量％以下の
（メタ）アクリル酸と、85重量％以上の（メタ）アクリ
ル酸エステル及び重合性のビニルモノマーとから成って
いる。(Prior Art) A general composition of an acrylic pressure-sensitive adhesive is composed of 15% by weight or less of (meth) acrylic acid, and 85% by weight or more of (meth) acrylic acid ester and a polymerizable vinyl monomer. .
ここで添加される（メタ）アクリル酸は、粘着剤の粘着
力と凝集力とを向上させるとともに、カルボキシル基が
架橋点となり粘着剤内部に架橋構造が形成される。The (meth) acrylic acid added here improves the adhesive force and cohesive force of the pressure-sensitive adhesive, and at the same time, the carboxyl group serves as a crosslinking point to form a crosslinked structure inside the pressure-sensitive adhesive.
（メタ）アクリル酸の添加量が増加すると、アクリル系
粘着剤のガラス転移温度（Tg）が上昇し、内部凝集力が
向上するが、逆に初期接着性（タック）は低下する。When the amount of (meth) acrylic acid added increases, the glass transition temperature (Tg) of the acrylic pressure-sensitive adhesive increases and the internal cohesive force improves, but on the contrary, the initial adhesiveness (tack) decreases.
一方、該粘着剤中に含有された（メタ）アクリル酸等の
カルボキシル基が、加水分解され易い被着体や支持体と
長期間接触した状態で置かれ、且つ水分が共存する場合
には、該カルボキシル基はアクリル系粘着剤の被着体や
支持体が加水分解するのを促進することが知られてい
る。On the other hand, when the carboxyl group such as (meth) acrylic acid contained in the pressure-sensitive adhesive is placed in a state of being in contact with an adherend or a support that is easily hydrolyzed for a long period of time, and water coexists, It is known that the carboxyl group promotes hydrolysis of the adherend and the support of the acrylic pressure-sensitive adhesive.
そこで、被着体や支持体に加水分解を起こす恐れのない
アクリル系粘着剤組成物として、特開昭59−111114号公
報には、（メタ）アクリル酸を含まないアクリル系粘着
剤組成物、即ち、アクリル酸ブチルとメタクリル酸ベン
ジルとメタクリル酸２−ヒドロキシエチルとを共重合し
たアクリル系粘着剤組成物が開示されている。Therefore, as an acrylic pressure-sensitive adhesive composition that does not cause hydrolysis on an adherend or a support, JP-A-59-111114 discloses a (meth) acrylic acid-free acrylic pressure-sensitive adhesive composition, That is, an acrylic pressure-sensitive adhesive composition obtained by copolymerizing butyl acrylate, benzyl methacrylate, and 2-hydroxyethyl methacrylate is disclosed.
しかしながら、上述の（メタ）アクリル酸を含まないア
クリル系粘着剤組成物は、加水分解され易い被着体、例
えば、三酢酸セルロースフィルムに対し、加水分解を抑
制する性能は優れているものの、粘着剤として要求され
る各種性能、特に内部凝集力と粘着力との両性能を同時
に満足させることが難しいという問題があった。However, the above-mentioned acrylic pressure-sensitive adhesive composition containing no (meth) acrylic acid is an adherend that is easily hydrolyzed, for example, a cellulose triacetate film, although the performance of suppressing hydrolysis is excellent. There is a problem that it is difficult to simultaneously satisfy various performances required as an agent, especially both performances of internal cohesive strength and adhesive strength.
特に、該粘着剤が被着状態で高温下に置かれた場合は、
粘着剤層にずれ、発泡、剥離が起こり易く、高信頼性が
要求される光学用途で使用することが難かしいという問
題点もあった。Especially when the adhesive is placed under high temperature in the adhered state,
There is also a problem that the pressure-sensitive adhesive layer is liable to be displaced, foamed, and peeled off, and it is difficult to use it for optical applications requiring high reliability.
又、OH基を架橋点とし、イソシアネートと架橋反応させ
た場合は、イソシアネートの適正添加量が極めて狭い範
囲に限られるので、粘着剤の性能を制御するのが難しい
という問題点もあった。Further, when the OH group is used as a cross-linking point and a cross-linking reaction with isocyanate is carried out, there is a problem that it is difficult to control the performance of the pressure-sensitive adhesive because the proper amount of isocyanate is limited to a very narrow range.
（発明が解決しようとする課題） 本発明は、アクリル酸エステル及び該アクリル酸エステ
ルと共重合可能なカルボキシル基含有化合物からなるア
クリル系粘着剤に、第三級アミンをラジカル共重合させ
ることにより、該アクリル系粘着剤中に存在するカルボ
キシル基によって被着体や支持体に加水分解が起こるの
を阻止し、粘着力、凝集力及び耐久性に優れたアクリル
系粘着剤組成物を提供することを主旨とする。(Problems to be Solved by the Invention) The present invention provides an acrylic pressure-sensitive adhesive composed of an acrylic acid ester and a carboxyl group-containing compound copolymerizable with the acrylic acid ester, by radically copolymerizing a tertiary amine, It is intended to provide an acrylic pressure-sensitive adhesive composition having excellent adhesion, cohesive force and durability by preventing hydrolysis of an adherend or a support due to a carboxyl group present in the acrylic pressure-sensitive adhesive. The main idea.
（課題を解決するための手段） 本発明のアクリル系粘着剤組成物は、上記問題点を解決
するためになされたものであり、（メタ）アクリル酸エ
ステル65〜96重量％、該（メタ）アクリル酸エステルと
共重合可能なカルボキシル基含有化合物３〜15重量％及
びビニル基を有する第三級アミン１〜20重量％をラジカ
ル共重合することにより、上記目的が達成される。(Means for Solving the Problems) The acrylic pressure-sensitive adhesive composition of the present invention is made to solve the above-mentioned problems, and comprises (meth) acrylic acid ester 65 to 96% by weight, The above object can be achieved by radically copolymerizing 3 to 15% by weight of a carboxyl group-containing compound copolymerizable with an acrylate ester and 1 to 20% by weight of a tertiary amine having a vinyl group.
本発明で使用される（メタ）アクリル酸エステルとは、
アクリル酸エステル又はメタクリル酸エステルであっ
て、例えば、（メタ）アクリル酸ブチル、（メタ）アク
リル酸２−エチルヘキシル、（メタ）アクリル酸イソオ
クチル、（メタ）アクリル酸イソノニル、（メタ）アク
リル酸オクチル、（メタ）アクリル酸デシル、（メタ）
アクリル酸ベンジル、（メタ）アクリル酸２−ヒドロキ
シエチル等が好適に使用される。The (meth) acrylic acid ester used in the present invention is
Acrylic acid ester or methacrylic acid ester, for example, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, octyl (meth) acrylate, Decyl (meth) acrylate, (meth)
Benzyl acrylate, 2-hydroxyethyl (meth) acrylate and the like are preferably used.
本発明で使用される（メタ）アクリル酸エステルと共重
合可能なカルボキシル基含有化合物としては、例えば、
アクリル酸、メタクリル酸、イタコン酸、クロトン酸、
マレイン酸等が挙げられる。Examples of the carboxyl group-containing compound copolymerizable with (meth) acrylic acid ester used in the present invention include:
Acrylic acid, methacrylic acid, itaconic acid, crotonic acid,
Maleic acid etc. are mentioned.
本発明で使用されるビニル基を有する第三級アミンとし
ては、例えば、（メタ）アクリル酸ジメチルアミノエチ
ル、（メタ）アクリル酸ジメチルアミノエチル、ジメチ
ルアミノプロピル（メタ）アクリルアミド等が好適に使
用される。As the tertiary amine having a vinyl group used in the present invention, for example, dimethylaminoethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylamide and the like are preferably used. It
本発明のアクリル系粘着剤組成物は、上記（メタ）アク
リル酸エステル、カルボキシル基含有化合物及び第三級
アミンをラジカル共重合したものであって、カルボキシ
ル基含有化合物の比率は小さくなると粘着剤の凝集力が
低下し、逆に多くなると粘着力が低下すると共に、被着
体や支持体の加水分解を促進するようになるので、３〜
15重量％に限定されるのであり、第三級アミンの比率は
小さくなるとカルボキシ基含有化合物による加水分解を
抑止する効果が低下し、逆に多くなると粘着剤が軟らか
くなり、粘着力や凝集力が低下するので１〜20重量％に
限定され、残りの65〜96重量％が（メタ）アクリル酸エ
ステルである。The acrylic pressure-sensitive adhesive composition of the present invention is a radical copolymerization of the above-mentioned (meth) acrylic acid ester, a carboxyl group-containing compound and a tertiary amine, and when the ratio of the carboxyl group-containing compound becomes small, When the cohesive force is reduced and, conversely, when the cohesive force is increased, the adhesive force is reduced and the hydrolysis of the adherend or the support is promoted.
Since it is limited to 15% by weight, if the ratio of the tertiary amine becomes small, the effect of suppressing the hydrolysis by the carboxy group-containing compound decreases, and conversely if it becomes large, the adhesive becomes soft and the adhesive force and cohesive force are Since it decreases, it is limited to 1 to 20% by weight, and the remaining 65 to 96% by weight is (meth) acrylic acid ester.
本発明の粘着剤組成物の凝集力を向上させるために、更
に（メタ）アクリル酸エステルと共重合可能なビニルエ
ステル、例えば、酢酸ビニル、塩化ビニル、塩化ビニリ
デン、アクリロニトリル、スチレン等を共重合させても
よい。In order to improve the cohesive strength of the pressure-sensitive adhesive composition of the present invention, a vinyl ester copolymerizable with (meth) acrylic acid ester, for example, vinyl acetate, vinyl chloride, vinylidene chloride, acrylonitrile, styrene or the like is copolymerized. May be.
本発明のアクリル粘着剤組成物のラジカル共重合方法
は、任意の方法が採用されてよく、例えば、溶液重合、
塊状重合、エマルジョン重合等が挙げられる。Radical copolymerization method of the acrylic pressure-sensitive adhesive composition of the present invention, any method may be adopted, for example, solution polymerization,
Examples include bulk polymerization and emulsion polymerization.
重合開始剤としては、過酸化物系、アゾ系化合物等従来
公知の任意のものが使用しうるが、光又は放射線等を照
射して重合してもよい。As the polymerization initiator, any conventionally known one such as a peroxide type compound or an azo type compound can be used, but it may be polymerized by irradiation with light or radiation.
又、分子量を調節するために、適当な連鎖移動剤、例え
ば、ラウリルメルカプタン等を使用してもよい。A suitable chain transfer agent such as lauryl mercaptan may be used to control the molecular weight.
更に、幅広い粘着物性を得るために、必要に応じて、可
塑剤、粘着付与剤、劣化防止剤等が添加されてもよい。Furthermore, in order to obtain a wide range of adhesive properties, a plasticizer, a tackifier, a deterioration inhibitor, etc. may be added as necessary.
（作用） 本発明のアクリル系粘着剤組成物は、（メタ）アクリル
酸エステル、該（メタ）アクリル酸エステルと共重合可
能なカルボキシル基含有化合物、及び第三級アミンがラ
ジカル共重合されているので、該カルボキシル基含有化
合物のカルボキシル基による加水分解が抑制される。(Function) In the acrylic pressure-sensitive adhesive composition of the present invention, a (meth) acrylic acid ester, a carboxyl group-containing compound copolymerizable with the (meth) acrylic acid ester, and a tertiary amine are radically copolymerized. Therefore, the hydrolysis of the carboxyl group-containing compound by the carboxyl group is suppressed.
又、本発明による粘着剤が、例えば、三酢酸セルロース
のような被着体や支持体と接触し、これを加水分解して
も、その際遊離した酢酸を第三級アミンが補足し、該酢
酸により加水分解が促進されるのを防止する。Further, when the pressure-sensitive adhesive according to the present invention is brought into contact with an adherend such as cellulose triacetate or a support and hydrolyzes it, the acetic acid liberated at that time is supplemented by a tertiary amine, Prevents accelerated hydrolysis by acetic acid.
（実施例） 以下に本発明の実施例について述べる。(Examples) Examples of the present invention will be described below.
実施例１〜６、比較例 （１）アクリル共重合体の調製 還流器及び撹拌器が設置されたフラスコ中に、表２に示
した所定量のアクリル酸ブチル、アクリル酸、ジメチル
アミノエチルアクリレート、過酸化ベンゾイル及び酢酸
エチルを添加して均一に混合した後、窒素気流中で撹拌
しながら還流温度で６時間ラジカル共重合しアクリル共
重合体溶液を調製した。Examples 1 to 6 and Comparative Example (1) Preparation of Acrylic Copolymer A predetermined amount of butyl acrylate, acrylic acid, dimethylaminoethyl acrylate shown in Table 2 was placed in a flask equipped with a reflux condenser and a stirrer. After adding benzoyl peroxide and ethyl acetate and mixing them uniformly, radical copolymerization was carried out at a reflux temperature for 6 hours while stirring in a nitrogen stream to prepare an acrylic copolymer solution.
（２）アクリル系粘着剤組成物の調製 上記アクリル共重合体溶液を固形分が25重量％となるよ
うに酢酸エチルで希釈した後、該共重合体の固形分100
重量部に、トリイソシアネート２重量部を添加、撹拌し
アクリル系粘着剤組成物を調製した。(2) Preparation of acrylic pressure-sensitive adhesive composition The acrylic copolymer solution was diluted with ethyl acetate so that the solid content was 25% by weight, and then the solid content of the copolymer was 100%.
2 parts by weight of triisocyanate was added to parts by weight and stirred to prepare an acrylic pressure-sensitive adhesive composition.
（３）アクリル粘着剤ラミネートの作成 （２）で調製したアクリル系粘着剤組成物を、シリコン
処理した38μｍ厚のポリエステルフィルム上に、乾燥後
の厚さが25μｍになるようにアプリケーターで塗工し、
オーブン中で５分間乾燥させた後、50μｍ厚の三酢酸セ
ルロースフィルムをラミネーターで貼り合わせ、アクリ
ル粘着剤ラミネート（ａ）を作成した。(3) Preparation of acrylic pressure-sensitive adhesive laminate The acrylic pressure-sensitive adhesive composition prepared in (2) was coated on a silicon-treated 38 μm thick polyester film with an applicator so that the thickness after drying would be 25 μm. ,
After drying in an oven for 5 minutes, a 50 μm thick cellulose triacetate film was laminated with a laminator to prepare an acrylic pressure-sensitive adhesive laminate (a).
又、前記三酢酸セルロースフィルムの代わりに50μｍ厚
のポリエステルフィルムをラミネーターで貼り合わせ、
アクリル粘着剤ラミネート（ｂ）を作成した。Also, instead of the cellulose triacetate film, a 50 μm-thick polyester film is laminated with a laminator,
An acrylic adhesive laminate (b) was created.
（４）物件の測定 ｉ）加水分解による外観試験 （３）で調製したアクリル粘着剤ラミネート（ａ）を一
週間放置後、50×100mmの大きさに切断し、シリコン処
理したポリエステルフィルムを剥離した後、剥離面に75
×150mmのガラス板を気泡の入らぬようにラミネーター
で貼合わせて試験片とした。(4) Measurement of property i) Hydrolysis appearance test After leaving the acrylic pressure-sensitive adhesive laminate (a) prepared in (3) for one week, it was cut into a size of 50 × 100 mm, and the silicone-treated polyester film was peeled off. After that, 75 on the release surface
A glass plate of × 150 mm was laminated with a laminator so as to prevent air bubbles from entering, to obtain a test piece.
該試験片をガラススタンドに立て、80℃、RH90％の恒温
恒湿槽中に、それぞれ、500、750、1000、1250及び1500
時間放置した後、加水分解による外観の変化を肉眼で観
察し、表１に示た外観の変化に対応する評価点を表３に
示した。The test piece is placed on a glass stand and placed in a constant temperature and humidity chamber at 80 ° C. and RH 90%, 500, 750, 1000, 1250 and 1500, respectively.
After standing for a period of time, changes in appearance due to hydrolysis were visually observed, and evaluation points corresponding to the changes in appearance shown in Table 1 are shown in Table 3.
ii）90℃剪断接着力試験 （３）で調製したアクリル粘着剤ラミネート（ｂ）を15
×100mmの大きさに切断し、シリコン処理したポリエス
テルフィルムを剥離した後、剥離面にガラス板が15×15
mmの面積で接着するように、重さ2kgのローラーを一往
復させて圧着した後、粘着剤が露出した部分にポリエス
テルフィルムを貼り合わせ試験片とした。 ii) 90 ℃ shear adhesive strength test 15 Acrylic adhesive laminate (b) prepared in (3)
After cutting to a size of 100 mm and peeling the siliconized polyester film, the glass surface is 15 × 15 on the peeling surface.
A roller having a weight of 2 kg was moved back and forth once so as to be bonded in an area of mm, and then a polyester film was attached to a portion where the adhesive was exposed to obtain a test piece.
該試験片を90℃の恒温槽に２時間放置した後、試験片を
恒温槽付インストロン型引張試験機で90℃に保ちなが
ら、1mm/分の速度で180度方向に引張り、剪断接着力を
測定し、その結果を表３に示した。After the test piece was left in a constant temperature bath of 90 ° C for 2 hours, the test piece was kept at 90 ° C with an Instron type tensile tester with a constant temperature bath, and pulled in a 180 ° direction at a speed of 1 mm / min to give a shear adhesive force. Was measured and the results are shown in Table 3.
（発明の効果） 本発明のアクリル系粘着剤組成物は、（メタ）アクリル
酸エステル、該（メタ）アクリル酸エステルと共重合可
能なカルボキシ基含有化合物及び第三級アミンがラジカ
ル共重合されているので、粘着力、凝集力、耐熱性等の
性能が優れ、被着体や支持体が加水分解することがな
い。 (Effects of the Invention) The acrylic pressure-sensitive adhesive composition of the present invention is obtained by radically copolymerizing a (meth) acrylic acid ester, a carboxy group-containing compound copolymerizable with the (meth) acrylic acid ester, and a tertiary amine. Therefore, the adhesiveness, cohesive force, heat resistance and other properties are excellent, and the adherend and the support are not hydrolyzed.
Claims (1)
％、該（メタ）アクリル酸エステルと共重合可能なカル
ボキシル基含有化合物３〜15重量％及びビニル基を有す
る第三級アミン１〜20重量％をラジカル共重合してなる
アクリル系粘着剤組成物。1. A (meth) acrylic acid ester of 65 to 96% by weight, a carboxyl group-containing compound copolymerizable with the (meth) acrylic acid ester of 3 to 15% by weight, and a tertiary amine having a vinyl group of 1 to 20. An acrylic pressure-sensitive adhesive composition obtained by radical-copolymerizing the amount by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63152591A JPH0798926B2 (en) | 1988-06-21 | 1988-06-21 | Acrylic adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63152591A JPH0798926B2 (en) | 1988-06-21 | 1988-06-21 | Acrylic adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH023481A JPH023481A (en) | 1990-01-09 |
| JPH0798926B2 true JPH0798926B2 (en) | 1995-10-25 |
Family
ID=15543788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63152591A Expired - Fee Related JPH0798926B2 (en) | 1988-06-21 | 1988-06-21 | Acrylic adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0798926B2 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5340649B2 (en) * | 2007-10-22 | 2013-11-13 | 日東電工株式会社 | Optical film pressure-sensitive adhesive composition, optical film pressure-sensitive adhesive layer, production method thereof, pressure-sensitive adhesive optical film, and image display device |
| EP2053109A1 (en) | 2007-10-22 | 2009-04-29 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical film, pressure-sensitive adhesive layer for optical film, production method thereof, pressure-sensitive adhesive optical film and image display |
| EP2072552A3 (en) * | 2007-12-20 | 2009-07-29 | Nitto Denko Corporation | Pressure-sensitive adhesive composition for optical films, pressure-sensitive adhesive optical film and image display |
| JP5379409B2 (en) | 2008-02-15 | 2013-12-25 | 日東電工株式会社 | Adhesive composition for optical film, adhesive optical film, and image display device |
| JP5379410B2 (en) | 2008-03-14 | 2013-12-25 | 日東電工株式会社 | Adhesive composition for optical film, adhesive optical film, and image display device |
| US9133368B2 (en) | 2011-08-31 | 2015-09-15 | Lintec Corporation | Adhesive sheet |
| WO2014051106A1 (en) | 2012-09-28 | 2014-04-03 | リンテック株式会社 | Adhesive sheet and method for manufacturing adhesive sheet |
| JP6291323B2 (en) | 2014-04-02 | 2018-03-14 | リンテック株式会社 | Adhesive sheet and method for producing adhesive sheet |
| JP6291322B2 (en) | 2014-04-02 | 2018-03-14 | リンテック株式会社 | Adhesive sheet and method for producing adhesive sheet |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52121644A (en) * | 1976-04-06 | 1977-10-13 | Nagoya Yukagaku Kogyo Kk | Adhesive composition and adhesive tape |
-
1988
- 1988-06-21 JP JP63152591A patent/JPH0798926B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52121644A (en) * | 1976-04-06 | 1977-10-13 | Nagoya Yukagaku Kogyo Kk | Adhesive composition and adhesive tape |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH023481A (en) | 1990-01-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |