JPH05140510A - Photopolymerizable adhesive composition, pressure-sensitive adhesive using the same and bonding sheets using the adhesive - Google Patents
Photopolymerizable adhesive composition, pressure-sensitive adhesive using the same and bonding sheets using the adhesiveInfo
- Publication number
- JPH05140510A JPH05140510A JP3334214A JP33421491A JPH05140510A JP H05140510 A JPH05140510 A JP H05140510A JP 3334214 A JP3334214 A JP 3334214A JP 33421491 A JP33421491 A JP 33421491A JP H05140510 A JPH05140510 A JP H05140510A
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- pressure
- sensitive adhesive
- parts
- weight
- 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.)
- Granted
Links
Landscapes
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は、アルキル(メタ)アク
リレ―ト単量体などを含む光重合性接着剤組成物と、こ
の接着剤組成物を光重合して感圧接着性および凝集力を
付与した感圧性接着剤と、この感圧性接着剤を基材の片
面または両面に設けてシ―ト状やテ―プ状などの形態と
した接着シ―ト類に関するものである。FIELD OF THE INVENTION The present invention relates to a photopolymerizable adhesive composition containing an alkyl (meth) acrylate monomer and the like, and pressure-sensitive adhesiveness and cohesive force by photopolymerizing this adhesive composition. The present invention relates to a pressure-sensitive adhesive provided with a pressure-sensitive adhesive, and an adhesive sheet in which the pressure-sensitive adhesive is provided on one surface or both surfaces of a base material to form a sheet or tape.
【0002】[0002]
【従来の技術】アルキル(メタ)アクリレ―ト単量体を
主成分とし、これにアクリル酸などの極性基含有単量体
を加えた単量体混合物を共重合させて得られる、アクリ
ル系の感圧性接着剤は、既に公知である。2. Description of the Related Art An acrylic (meth) acrylate monomer as a main component, which is obtained by copolymerizing a monomer mixture in which a polar group-containing monomer such as acrylic acid is added, is obtained. Pressure sensitive adhesives are already known.
【0003】アクリル系の感圧性接着剤の製造に際し、
アクリル系ポリマ―の重合に効果のある多量の溶剤を用
いることが多いが、この多量の溶剤の安全性と環境上の
制約から、最近では、エマルジヨン重合や紫外線照射に
よる光重合が多く用いられつつある。特に、光重合した
感圧性接着剤は、その製造工程で溶剤を全く使用しない
ため、安全性と環境改善の効果がある。In the production of acrylic pressure-sensitive adhesives,
A large amount of solvent effective for polymerization of acrylic polymers is often used, but recently, due to the safety and environmental restrictions of this large amount of solvent, emulsion polymerization and photopolymerization by ultraviolet irradiation have been widely used. is there. In particular, the photopolymerized pressure-sensitive adhesive has the effect of improving safety and the environment because it does not use any solvent in its manufacturing process.
【0004】この安全性と環境改善の観点とは別に、近
年、感圧性接着剤の使用範囲が広がり、これまで屋内で
のみ用いられていた家電用品などが屋外でも用いられる
ようになり、これに伴い持ち運びによる衝撃を頻繁に受
けたり、屋外に近い状態で保存されることが多くなつて
きた。このため、要求される特性も高度化する傾向にあ
り、特に、使用される温度範囲が広がり、今まで以上に
低温や高温での接着特性の向上が必要となつており、ま
た−10〜30℃の通常の温度での接着特性も当然要求
される。Apart from this viewpoint of safety and environmental improvement, the range of use of pressure-sensitive adhesives has expanded in recent years, and household electric appliances and the like, which have been used only indoors until now, are now used outdoors. As a result, they are often subjected to the impact of being carried around, and are often stored near the outdoors. For this reason, the required properties also tend to be advanced, and in particular, the temperature range used is widened, and it is necessary to improve the adhesive properties at lower and higher temperatures than ever before. Adhesive properties at normal temperatures of ° C are also naturally required.
【0005】この要求に対し、アクリル系ポリマ―のガ
ラス転移温度を低くして、低温での接着特性を向上させ
ることが知られているが、この場合、通常の温度での凝
集力が低下する傾向があり、好ましくない。In response to this requirement, it is known that the glass transition temperature of the acrylic polymer is lowered to improve the adhesive property at low temperature, but in this case, the cohesive force at normal temperature is lowered. There is a tendency and it is not preferable.
【0006】特開昭57−47308号公報には、アル
キル(メタ)アクリレ―ト単量体100重量部に、実質
上飽和の粘着付与樹脂重合体50〜250重量部と、上
記の単量体に溶解した非晶質エラストマ―ブロツク共重
合体4〜150重量部を加えた光重合型の感圧性接着剤
が示されている。しかし、粘着付与樹脂重合体の使用量
が非常に多いために、ポリマ―のガラス転移温度を著し
く増大させ、低温での耐衝撃性が低下する問題がある。JP-A-57-47308 discloses that 100 parts by weight of an alkyl (meth) acrylate monomer, 50 to 250 parts by weight of a substantially saturated tackifying resin polymer and the above-mentioned monomer are used. A photopolymerizable pressure-sensitive adhesive containing 4 to 150 parts by weight of an amorphous elastomer block copolymer dissolved in the above is shown. However, since the amount of the tackifying resin polymer used is very large, there is a problem that the glass transition temperature of the polymer is remarkably increased and the impact resistance at low temperature is lowered.
【0007】特開平2−45580号公報、特開平2−
47182号公報には、アクリル系ポリマ―に、このポ
リマ―よりもガラス転移温度の低い炭化水素エラストマ
―を加えた感圧性接着剤が示されている。しかし、上記
の炭化水素エラストマ―の使用は、低温での耐衝撃性に
好結果を与えるが、耐老化性、耐熱性、高温での接着特
性に問題をきたし、使用範囲の拡大に伴い要求される高
度の接着特性を必ずしも満足できるものではない。Japanese Unexamined Patent Publication Nos. 2-45580 and 2-
Japanese Patent No. 47182 discloses a pressure-sensitive adhesive obtained by adding a hydrocarbon elastomer having a glass transition temperature lower than that of an acrylic polymer to an acrylic polymer. However, although the use of the above-mentioned hydrocarbon elastomer gives good results in impact resistance at low temperature, it causes problems in aging resistance, heat resistance, and adhesive properties at high temperature, and is required as the usage range is expanded. It is not always possible to satisfy the high level of adhesive properties.
【0008】特開昭63−72532号公報には、弾性
非粘着性中空熱可塑性重合体球を含ませた感圧性接着剤
被覆シ―ト材料が示されているが、低温での接着特性が
十分とは言えない。特開平1−284572号公報に
は、電離放射線硬化型粘着剤に有機樹脂微粉末を含ませ
たものが示されているが、低温での接着力や耐衝撃性の
面で満足できるものではない。Japanese Unexamined Patent Publication (Kokai) No. 63-72532 discloses a pressure-sensitive adhesive-coated sheet material containing elastic non-adhesive hollow thermoplastic polymer spheres, which has adhesive properties at low temperatures. Not enough. Japanese Unexamined Patent Publication (Kokai) No. 1-284572 discloses an ionizing radiation-curable pressure-sensitive adhesive containing an organic resin fine powder, but it is not satisfactory in terms of adhesive strength and impact resistance at low temperatures. ..
【0009】[0009]
【発明が解決しようとする課題】本発明は、上記従来の
事情に鑑み、光重合型のアクリル系感圧性接着剤におい
て、低温から高温までの接着特性が良好であると共に、
低温での耐衝撃性にすぐれたものを得ることを目的とし
ている。In view of the above-mentioned conventional circumstances, the present invention provides a photopolymerization type acrylic pressure-sensitive adhesive having excellent adhesive properties from low temperature to high temperature, and
The purpose is to obtain a material that has excellent impact resistance at low temperatures.
【0010】[0010]
【課題を解決するための手段】本発明者らは、上記の目
的を達成するために鋭意検討した結果、光重合させるべ
き接着剤組成物中にシリコ―ンゴム粒子を添加したとき
に、低温から高温までの接着特性が良好であるうえに、
低温での耐衝撃性にもすぐれた感圧性接着剤が得られる
ことを知り、本発明を完成するに至つた。Means for Solving the Problems As a result of intensive studies for achieving the above-mentioned object, the present inventors have found that when the silicone rubber particles are added to the adhesive composition to be photopolymerized, it is In addition to having good adhesive properties up to high temperatures,
The inventors have found that a pressure-sensitive adhesive having excellent impact resistance at low temperatures can be obtained, and have completed the present invention.
【0011】すなわち、本発明は、つぎのa〜c三成
分; a)アルキル基が平均1〜14個の炭素原子を有するア
ルキル(メタ)アクリレ―ト単量体を主成分とする主単
量体70〜99重量%と、極性基含有の共重合性単量体
30〜1重量%とからなる単量体混合物100重量部 b)シリコ―ゴム粒子2〜60重量部 c)光重合開始剤0.01〜5重量部 を必須成分として含有することを特徴とする光重合性接
着剤組成物に係るものである。That is, the present invention provides the following three components a to c: a) a main monomer containing an alkyl (meth) acrylate monomer whose alkyl group has an average of 1 to 14 carbon atoms as a main component. 100 to 100 parts by weight of a monomer mixture consisting of 70 to 99% by weight of a copolymer and 30 to 1% by weight of a polar group-containing copolymerizable monomer b) Silicon rubber particles 2 to 60 parts by weight c) Photopolymerization initiator The present invention relates to a photopolymerizable adhesive composition containing 0.01 to 5 parts by weight as an essential component.
【0012】また、本発明は、上記の光重合性接着剤組
成物を、紫外線などの光照射により光重合させて、感圧
接着性および凝集力を付与したアクリル系感圧性接着剤
と、さらにこの感圧性接着剤を基材の片面または両面に
設けてシ―ト状やテ―プ状などの形態とした接着シ―ト
類に係るものである。The present invention also provides an acrylic pressure-sensitive adhesive having pressure-sensitive adhesiveness and cohesive force obtained by photopolymerizing the above-mentioned photopolymerizable adhesive composition by irradiation with light such as ultraviolet rays. The present invention relates to an adhesive sheet in which the pressure-sensitive adhesive is provided on one surface or both surfaces of a base material so as to have a sheet shape or a tape shape.
【0013】[0013]
【発明の構成・作用】本発明におけるa成分としての単
量体混合物は、アルキル(メタ)アクリレ―ト単量体を
主成分とする主単量体と、極性基含有の共重合性単量体
との混合物からなるものであり、前者の主単量体として
は、主成分としてのアルキル(メタ)アクリレ―ト単量
体のほかに、酢酸ビニル、スチレンなどの一般のアクリ
ル系感圧性接着剤の改質用単量体として知られる各種の
ビニル系単量体を、主単量体中、通常30重量%以下の
割合で使用することができる。The monomer mixture as the component a in the present invention comprises a main monomer mainly comprising an alkyl (meth) acrylate monomer and a polar group-containing copolymerizable monomer. It is composed of a mixture with the body, and the former main monomer includes, in addition to the alkyl (meth) acrylate monomer as the main component, general acrylic pressure-sensitive adhesives such as vinyl acetate and styrene. Various vinyl-based monomers known as modifying monomers for agents are usually used in the main monomer in an amount of 30% by weight or less.
【0014】アルキル(メタ)アクリレ―ト単量体とし
ては、たとえば、メチル(メタ)アクリレ―ト、n−ブ
チル(メタ)アクリレ―ト、2−エチルヘキシル(メ
タ)アクリレ―ト、イソオクチル(メタ)アクリレ―
ト、イソノニル(メタ)アクリレ―トなどのアルキル基
の炭素数が1〜14の範囲にあるものがいずれも使用可
能である。Examples of the alkyl (meth) acrylate monomer include, for example, methyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate. Acryl
Any of those having an alkyl group having a carbon number of 1 to 14 such as bisphenol and isononyl (meth) acrylate can be used.
【0015】極性基含有の共重合性単量体としては、
(メタ)アクリル酸、イタコン酸、2−アクリルアミド
プロパンスルホン酸などの不飽和酸、2−ヒドロキシエ
チル(メタ)アクリレ―ト、2−ヒドロキシプロピル
(メタ)アクリレ―トなどの水酸基含有単量体などが用
いられる。The polar group-containing copolymerizable monomer includes
Unsaturated acids such as (meth) acrylic acid, itaconic acid and 2-acrylamidopropanesulfonic acid, hydroxyl group-containing monomers such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate Is used.
【0016】アルキル(メタ)アクリレ―ト単量体を主
成分とする主単量体と、極性基含有の共重合性単量体と
の使用割合としては、前者が70〜99重量%、後者が
30〜1重量%となるようにすべきであり、特に好まし
くは前者が90〜98重量%、後者が10〜2重量%と
なるようにするのがよい。これらの範囲外では、接着特
性上好ましい結果が得られない。The proportion of the main monomer containing an alkyl (meth) acrylate monomer as the main component and the polar group-containing copolymerizable monomer is 70 to 99% by weight in the former case and the latter in the latter case. Should be 30 to 1% by weight, particularly preferably 90 to 98% by weight for the former and 10 to 2% by weight for the latter. Outside of these ranges, favorable results cannot be obtained in terms of adhesive properties.
【0017】本発明におけるb成分としてのシリコ―ン
ゴム粒子は、たとえば、ジメチルジクロロシランの加水
分解によるシラノ―ルの重縮合により、またジメチルシ
ロキサン単位の一部をビニル基で置換したものや、メチ
ルフエニルシロキサンを共重合することなどにより、得
られるもので、そのガラス転移温度としては、−100
〜−120℃程度のものである。市販品としては、たと
えば、東レ・ダウコ―ニング・シリコ―ン(株)製のト
レフイルE−500、トレフイルE−501などを挙げ
ることができる。The silicone rubber particles as the component b in the present invention are, for example, those obtained by polycondensation of silanol by hydrolysis of dimethyldichlorosilane, and those obtained by substituting a part of dimethylsiloxane units with vinyl groups or methyl. It is obtained by copolymerizing phenyl siloxane and has a glass transition temperature of -100.
It is about -120 ° C. Examples of commercially available products include Trefil E-500 and Trefil E-501 manufactured by Toray Dow Corning Silicone Co., Ltd.
【0018】このシリコ―ンゴム粒子は、種々の粒子形
状をとりうるが、好ましくは球状であるのがよい。平均
粒径は、この粒子を含む感圧性接着剤の層を基材の片面
または両面に設けて接着シ―ト類を作製する場合に、上
記層の厚さよりも小さい平均粒径となるようにするのが
よく、通常は1〜100μmの範囲から適宜設定するこ
とができる。The silicone rubber particles can have various particle shapes, but are preferably spherical. The average particle size should be smaller than the thickness of the layer when a pressure-sensitive adhesive layer containing the particles is provided on one or both sides of a substrate to produce adhesive sheets. It is preferable to set the thickness in a range of 1 to 100 μm.
【0019】このようなシリコ―ンゴム粒子を用いる
と、低温での接着力や耐衝撃性にすぐれ、かつ凝集力の
面でも満足できる感圧性接着剤を得ることが可能とな
る。このシリコ―ンゴム粒子の使用量としては、前記の
a成分100重量部あたり、通常2〜60重量部、好ま
しくは5〜35重量部とするのがよい。2重量部より少
ないと、上記の作用効果が得られず、また60重量部よ
り多くなると、通常の温度での接着特性が損なわれる。The use of such silicone rubber particles makes it possible to obtain a pressure-sensitive adhesive which has excellent adhesive strength and impact resistance at low temperatures, and which is satisfactory in terms of cohesive strength. The amount of the silicone rubber particles used is usually 2 to 60 parts by weight, preferably 5 to 35 parts by weight, per 100 parts by weight of the component a. If the amount is less than 2 parts by weight, the above-mentioned effects cannot be obtained, and if the amount is more than 60 parts by weight, the adhesive properties at normal temperature are impaired.
【0020】本発明におけるc成分の光重合開始剤とし
ては、ベンゾインメチルエ―テル、ベンゾインイソプロ
ピルエ―テルなどのベンゾインエ―テル、アニソ―ルメ
チルエ―テルなどの置換ベンゾインエ―テル、2・2−
ジエトキシアセトフエノン、2・2−ジメトキシ−2−
フエニルアセトフエノンなどの置換アセトフエノン、2
−メチル−2−ヒドロキシプロピオフエノンなどの置換
アルフア―ケト―ル、2−ナフタレンスルフオニルクロ
ライドなどの芳香族スルフオニルクロライド、1−フエ
ニル−1・1−プロパンジオン−2−(o−エトキシカ
ルボニル)−オキシムなどの光活性オキシムが用いられ
る。Examples of the c component photopolymerization initiator in the present invention include benzoin ether such as benzoin methyl ether and benzoin isopropyl ether, and substituted benzoin ether such as anisolemethyl ether, 2.2-
Diethoxyacetophenone, 2,2-dimethoxy-2-
Substituted acetophenones such as phenylacetophenones, 2
-Substituted alpha-ketols such as methyl-2-hydroxypropionenone, aromatic sulfonyl chlorides such as 2-naphthalene sulphonyl chloride, 1-phenyl-1. 1-propanedione-2- (o- Photoactive oximes such as ethoxycarbonyl) -oxime are used.
【0021】このような光重合開始剤の使用量は、前記
のa成分100重量部あたり、通常0.01〜5重量
部、好ましくは0.01〜2重量部とするのがよい。
0.01重量部より少ないと重合率が下がり、また5重
量部より多いと重合率は上がるが分子量が低下して凝集
力が不足する。The amount of such a photopolymerization initiator to be used is usually 0.01 to 5 parts by weight, preferably 0.01 to 2 parts by weight, per 100 parts by weight of the component a.
If the amount is less than 0.01 parts by weight, the polymerization rate will decrease. If the amount is more than 5 parts by weight, the polymerization rate will increase, but the molecular weight will decrease and the cohesive force will be insufficient.
【0022】本発明の光重合性接着剤組成物は、上記の
a〜c三成分のほかに、必要に応じて多官能アクリレ―
ト単量体を加えてもよい。この単量体としては、たとえ
ば、トリメチロ―ルプロパントリアクリレ―ト、ペンタ
エリスリト―ルテトラアクリレ―ト、1・2−エチレン
グリコ―ルジアクリレ―ト、1・6−ヘキサンジオ―ル
ジアクリレ―ト、1・12−ドデカンジオ―ルジアクリ
レ―トなどの2官能以上の多価アルキルアクリレ―ト単
量体が用いられる。The photopolymerizable adhesive composition of the present invention comprises, in addition to the above-mentioned three components a to c, a polyfunctional acrylate if necessary.
A monomer may be added. Examples of this monomer include trimethylol propane triacrylate, pentaerythritol tetraacrylate, 1.2-ethylene glycol diacrylate, 1.6-hexanediol diacrylate, 1. A bifunctional or higher-functional polyvalent alkyl acrylate monomer such as 12-dodecanediol diacrylate is used.
【0023】このような多官能アクリレ―ト単量体を用
いる場合の使用量としては、その官能基数などにより多
少異なるが、一般には、前記のa成分100重量部あた
り、0.1〜3重量部、好ましくは0.2〜2重量部と
するのがよい。このような範囲で多官能アクリレ―ト単
量体を用いると、上記単量体の架橋効果によつて良好な
凝集力が保持される。The amount of such a polyfunctional acrylate monomer used varies somewhat depending on the number of functional groups, etc., but is generally 0.1 to 3 parts by weight per 100 parts by weight of the component a. Parts, preferably 0.2 to 2 parts by weight. When the polyfunctional acrylate monomer is used in such a range, good cohesive force is maintained due to the crosslinking effect of the above monomer.
【0024】本発明の光重合性接着剤組成物は、上記a
〜c三成分を必須成分とし、必要により多官能アクリレ
―ト単量体を含むものであるが、その取り扱い上、a成
分の単量体混合物については、これをc成分の光重合開
始剤の一部を用いてある程度予備重合させておくことが
できる。The photopolymerizable adhesive composition of the present invention has the above a.
To c are essential components and, if necessary, a polyfunctional acrylate monomer, but in view of handling the monomer mixture of the component a, this is a part of the photopolymerization initiator of the component c. Can be used for pre-polymerization to some extent.
【0025】また、この光重合性接着剤組成物には、上
記の成分以外に、任意成分として、可塑剤、軟化剤、充
てん剤、顔料、染料、粘着付与樹脂などの従来公知の各
種の添加剤を、その光重合性を阻害しない範囲内で適宜
配合することができる。In addition to the above-mentioned components, various optional additives such as plasticizers, softeners, fillers, pigments, dyes, tackifying resins, etc., which have been publicly known, are added to the photopolymerizable adhesive composition. The agent can be appropriately blended within a range that does not impair the photopolymerizability.
【0026】本発明においては、このような光重合性接
着剤組成物を、被着体上に直接塗工するか、または一旦
剥離紙上に塗工したうえで、400〜2000mj/cm2
程度の紫外線を照射して、光重合させることにより、そ
れ自体感圧接着性を有する、粘着化されたアクリル系感
圧性接着剤とすることができる。In the present invention, such a photopolymerizable adhesive composition is directly coated on an adherend or once coated on a release paper, and then 400 to 2000 mj / cm 2
By irradiating a certain amount of ultraviolet rays and photopolymerizing, a pressure-sensitive acrylic pressure-sensitive adhesive having pressure-sensitive adhesive property can be obtained.
【0027】また、被着体や剥離紙上に塗工する代わり
に、ポリエステルフイルムなどの合成樹脂フイルムや繊
維基材などの各種基材を使用し、この基材の片面または
両面に塗設して、これを上記同様に光重合させることに
より、シ―ト状やテ―プ状などの形態とした接着シ―ト
類とすることができる。Further, instead of coating on an adherend or a release paper, various base materials such as a synthetic resin film such as a polyester film and a fiber base material are used, and the base material is coated on one side or both sides. By subjecting this to photopolymerization in the same manner as described above, it is possible to obtain an adhesive sheet in the form of a sheet, a tape or the like.
【0028】さらに、このような接着シ―ト類を得るに
あたり、感圧性接着剤の層を多層構造として、そのうち
の少なくとも一層を、本発明の接着剤組成物を光重合し
た層としてもよい。また、単層構造の感圧性接着剤の層
において、その一部だけを、本発明の接着剤組成物を光
重合した層で構成することもできる。Further, in obtaining such an adhesive sheet, the pressure-sensitive adhesive layer may have a multi-layer structure, and at least one of them may be a layer obtained by photopolymerizing the adhesive composition of the present invention. Further, in the pressure-sensitive adhesive layer having a single-layer structure, only a part thereof may be formed by a layer obtained by photopolymerizing the adhesive composition of the present invention.
【0029】このようにして得られる光重合したアクリ
ル系感圧性接着剤は、低温から高温までの接着特性が良
好で、しかも低温での耐衝撃性にすぐれるという特徴を
有している。この理由は必ずしも明らかではないが、シ
リコ―ンゴム粒子を均一に分散させた状態で光重合し
て、それ自体感圧接着性を有する、粘着化された感圧性
接着剤としているため、上記粒子に基づく接着特性や耐
衝撃性の改善作用が十分に発現されるためではないかと
思われる。The photopolymerized acrylic pressure-sensitive adhesive thus obtained is characterized in that it has good adhesive properties from low temperature to high temperature and is excellent in impact resistance at low temperature. The reason for this is not necessarily clear, but the silicone rubber particles are photopolymerized in a uniformly dispersed state to have a pressure-sensitive adhesive property, which is a pressure-sensitive adhesive that has been tackified. This is probably because the adhesive properties and impact resistance-improving action based on the above are sufficiently exhibited.
【0030】これに対し、たとえば、本発明のa成分に
相当する単量体混合物を用いて溶液重合によりアクリル
系ポリマ―を得、このポリマ―溶液にシリコ―ンゴム粒
子を均一に分散させて感圧性接着剤溶液を調製し、これ
を塗布乾燥して感圧性接着剤の層を形成したときには、
乾燥時にシリコ―ンゴム粒子の均一分散が損なわれるた
めか、低温から高温までの接着特性が上記本発明のもの
に比べてやや低下する傾向がみられるだけでなく、低温
での耐衝撃性がほとんど改良されず、本発明の目的を達
成できなくなる。On the other hand, for example, an acrylic polymer is obtained by solution polymerization using a monomer mixture corresponding to the component a of the present invention, and the silicone rubber particles are uniformly dispersed in the polymer solution to give a feeling. When a pressure-sensitive adhesive solution is prepared and applied and dried to form a pressure-sensitive adhesive layer,
Perhaps because the uniform dispersion of the silicone rubber particles is impaired during drying, the adhesive properties from low temperature to high temperature tend to be slightly lower than those of the present invention, and the impact resistance at low temperature is almost the same. Without improvement, the object of the present invention cannot be achieved.
【0031】[0031]
【発明の効果】以上のように、本発明では、アルキル
(メタ)アクリレ―ト単量体を主成分とした単量体混合
物に、光重合開始剤と共にシリコ―ンゴム粒子を特定量
含ませて、光重合させるようにしたことにより、低温か
ら高温までの接着特性が良好で、そのうえ低温での耐衝
撃性にすぐれたアクリル系感圧性接着剤とその接着シ―
ト類を得ることができる。As described above, according to the present invention, a monomer mixture containing an alkyl (meth) acrylate monomer as a main component contains a specific amount of silicone rubber particles together with a photopolymerization initiator. Since it is photopolymerized, it has good adhesive properties from low temperature to high temperature, and it has excellent impact resistance at low temperature.
You can get the kind.
【0032】[0032]
【実施例】つぎに、本発明の実施例を記載してより具体
的に説明する。なお、以下において、部とあるのは重量
部を意味する。また、接着テ―プの特性評価は、以下の
方法で行つた。EXAMPLES Next, examples of the present invention will be described to more specifically describe. In the following, "parts" means "parts by weight". The characteristics of the adhesive tape were evaluated by the following methods.
【0033】<接着力>JIS Z−1522に準じ、
被着体としてステンレス板を用いて、各温度下での接着
力(g/20mm幅)を測定した。<Adhesive strength> According to JIS Z-1522,
Using a stainless steel plate as an adherend, the adhesive force (g / 20 mm width) at each temperature was measured.
【0034】<対クリ―プ性ズレ距離>表面がBA仕上
げされたステンレス板(30mm×120mm×3.0mm)
を使用し、このステンレス板の長尺方向の一端に、接着
面積が20mm×10mmとなるように評価用サンプル(幅
10mm)を貼り合わせ、30分間放置したのち、40℃
の温度で20分間加熱処理した。つぎに、サンプルが貼
つてある方が下になるようにステンレス板を垂直に設定
し、サンプルの他端に500gの荷重をかけ、この状態
で40℃中での1時間当たりのステンレス板からのサン
プルのズレ距離をクリ―プ試験機で測定した。<Creapability deviation distance> Stainless steel plate with a BA finish on the surface (30 mm x 120 mm x 3.0 mm)
Using the above, a sample for evaluation (width 10 mm) was attached to one end of this stainless steel plate in the longitudinal direction so that the adhesion area was 20 mm × 10 mm, and the sample was left for 30 minutes, then at 40 ° C.
It heat-processed at the temperature of 20 minutes. Next, the stainless steel plate was set vertically so that the side where the sample was stuck was on the bottom, and a load of 500 g was applied to the other end of the sample. The shift distance of the sample was measured by a creep tester.
【0035】<耐低温衝撃性>ポリ塩化ビニル板(15
mm×150mm×3.0mm)に評価用サンプルを5Kgロ
―ラで圧着貼付し、これを塗装鋼板(100mm×300
mm×2.0mm)の中央部に評価用サンプルを内側にして
5Kgロ―ラで圧着貼付し、試験片とした。この試験片
を、23±1℃で24時間保存し、さらに−30℃で2
時間以上放置したのち、衝撃試験機(90度の角度から
試験片に衝撃を加えることができるJIS G−319
2に規定する等辺山形鋼を用いたもの)に、ポリ塩化ビ
ニル板を内側にして試験片取付け枠に取付け、90度
(π/2・rad)の角度から50回の衝撃を与えたと
きに、上記のポリ塩化ビニル板が試験片から落下するか
どうかを調べた。<Low temperature impact resistance> Polyvinyl chloride plate (15
mm × 150 mm × 3.0 mm), the evaluation sample is pressure-bonded with a 5 kg roller, and this is a coated steel plate (100 mm × 300 mm)
(mm × 2.0 mm), the sample for evaluation was placed on the inner side by pressure bonding with a 5 kg roller to give a test piece. The test piece was stored at 23 ± 1 ° C for 24 hours, and further stored at -30 ° C for 2 hours.
After leaving it for more than an hour, an impact tester (a test piece capable of applying an impact from a 90 degree angle to JIS G-319
(Equal helix angle steel specified in 2) is attached to the test piece mounting frame with the polyvinyl chloride plate inside and is given 50 shocks from an angle of 90 degrees (π / 2 · rad). It was examined whether the above polyvinyl chloride plate dropped from the test piece.
【0036】実施例1 2−エチルヘキシルアクリレ―ト90部、アクリル酸1
0部、2・2−ジメトキシ−2−フエニルアセトフエノ
ン(光重合開始剤)0.05部を、4つ口フラスコに投
入し、窒素雰囲気下で紫外線に暴露して部分的に光重合
させることにより、コ―テイング可能なシロツプ(粘度
30ポイズ)を得た。Example 1 90 parts of 2-ethylhexyl acrylate, acrylic acid 1
0 part, 0.05 parts of 2,2-dimethoxy-2-phenylacetophenone (photopolymerization initiator) were charged into a 4-neck flask and exposed to ultraviolet rays under a nitrogen atmosphere to partially photopolymerize. By this, a coatable syrup (viscosity 30 poise) was obtained.
【0037】この部分重合したシロツプ100部に、ト
リメチロ―ルプロパントリアクリレ―ト0.2部、追加
の光重合開始剤0.2部、平均粒径が3μmの球状のシ
リコ―ンゴム粒子〔東レ・ダウコ―ニング・シリコ―ン
(株)製のトレフイルE−500〕15部を、均一混合
して、光重合性接着剤組成物を調製した。To 100 parts of this partially polymerized syrup, 0.2 part of trimethylolpropane triacrylate, 0.2 part of additional photopolymerization initiator, spherical silicone rubber particles having an average particle size of 3 μm [ Toray Dow Corning Silicone KK-made TREFIL E-500] 15 parts were uniformly mixed to prepare a photopolymerizable adhesive composition.
【0038】この接着剤組成物を、低接着性剥離処理が
施された厚さが25μmのポリエチレンテレフタレ―ト
フイルムの上記剥離処理面に、塗工し、さらにこの上に
厚さが25μmのポリエチレンテレフタレ―トフイルム
を基材として被覆したのち、紫外線を1500mj/cm2
照射して光重合させて、接着剤層の厚さが400μmの
接着テ―プを得た。This adhesive composition was applied to the above-mentioned release-treated surface of a polyethylene terephthalate film having a thickness of 25 μm which had been subjected to a low-adhesion release treatment, and further, a polyethylene having a thickness of 25 μm was applied thereon. After coating with terephthalate film as the base material, it is exposed to ultraviolet rays at 1500 mj / cm 2
By irradiation and photopolymerization, an adhesive tape having an adhesive layer thickness of 400 μm was obtained.
【0039】実施例2 シリコ―ンゴム粒子として、平均粒径が10μmの球状
のシリコ―ンゴム粒子〔東レ・ダウコ―ニング・シリコ
―ン(株)製のトレフイルE−501〕15部を用いた
以外は、実施例1と同様にして光重合性接着剤組成物を
調製し、この組成物を用いて実施例1と同様にして接着
テ―プを作製した。Example 2 As the silicone rubber particles, 15 parts of spherical silicone rubber particles having an average particle size of 10 μm [Trefyl E-501 manufactured by Toray Dow Corning Silicone Co., Ltd.] were used. In the same manner as in Example 1, a photopolymerizable adhesive composition was prepared, and an adhesive tape was produced in the same manner as in Example 1 using this composition.
【0040】実施例3 イソデシルアクリレ―ト90部、アクリル酸10部、2
−ヒドロキシエチルアクリレ―ト2部、2・2−ジメト
キシ−2−フエニルアセトフエノン(光重合開始剤)
0.1部を、4つ口フラスコに投入し、窒素雰囲気下で
紫外線に暴露して部分的に光重合させることにより、コ
―テイング可能なシロツプ(粘度50ポイズ)を得た。
このシロツプを用いた以外は、実施例1と同様にして光
重合性接着剤組成物を調製し、この組成物を用いて実施
例1と同様にして接着テ―プを作製した。Example 3 90 parts of isodecyl acrylate, 10 parts of acrylic acid, 2
-Hydroxyethyl acrylate 2 parts, 2.2-dimethoxy-2-phenylacetophenone (photopolymerization initiator)
0.1 part was placed in a four-necked flask and exposed to ultraviolet rays in a nitrogen atmosphere to partially photopolymerize to obtain a coatable syrup (viscosity 50 poise).
A photopolymerizable adhesive composition was prepared in the same manner as in Example 1 except that this syrup was used, and an adhesive tape was prepared in the same manner as in Example 1 using this composition.
【0041】実施例4 2−エチルヘキシルアクリレ―ト90部、アクリル酸1
0部、2・2´−アゾビスイソブチロニトリル0.4
部、酢酸エチル250部を、4つ口フラスコに投入し、
窒素雰囲気下60℃で10時間重合して、重合体溶液を
得た。この重合体溶液に、ポリマ―100部に対して、
3官能のイソシアネ―ト化合物2部を添加して、感圧性
接着剤溶液を調製した。Example 4 90 parts of 2-ethylhexyl acrylate, acrylic acid 1
0 part, 2.2'-azobisisobutyronitrile 0.4
Parts, 250 parts of ethyl acetate are charged into a four-necked flask,
Polymerization was carried out at 60 ° C. for 10 hours in a nitrogen atmosphere to obtain a polymer solution. To this polymer solution, for 100 parts of polymer,
A pressure sensitive adhesive solution was prepared by adding 2 parts of a trifunctional isocyanate compound.
【0042】つぎに、この接着剤溶液を、低接着性剥離
処理が施された厚さが25μmのポリエチレンテレフタ
レ―トフイルム上に、乾燥後の厚さが25μmとなるよ
うに塗布し、40℃で5分間乾燥後、100℃で5分間
乾燥した。これを実施例3で得た接着テ―プの両面にラ
ミネ―トロ―ルで圧着したのち、100℃で2時間エ―
ジングを行い、3層構造を有する接着テ―プを得た。Next, this adhesive solution was applied to a polyethylene terephthalate film having a thickness of 25 μm and subjected to a low-adhesion peeling treatment so that the thickness after drying would be 25 μm, and the temperature was 40 ° C. After drying for 5 minutes at 100 ° C., it was dried for 5 minutes. This was adhered to both sides of the adhesive tape obtained in Example 3 with a laminator, and then heated at 100 ° C. for 2 hours.
Then, an adhesive tape having a three-layer structure was obtained.
【0043】比較例1 シリコ―ンゴム粒子を全く用いなかつた以外は、実施例
1と同様にして光重合性接着剤組成物を調製し、この組
成物を用いて実施例1と同様にして接着テ―プを作製し
た。Comparative Example 1 A photopolymerizable adhesive composition was prepared in the same manner as in Example 1 except that no silicone rubber particles were used. Adhesion was performed in the same manner as in Example 1 using this composition. A tape was made.
【0044】比較例2 シリコ―ンゴム粒子に代えて、弾性非粘着性中空熱可塑
性重合体球〔日本フイライト(株)製のエクスパンセル
551DE〕2部を用いた以外は、実施例1と同様にし
て光重合性接着剤組成物を調製し、この組成物を用いて
実施例1と同様にして接着テ―プを作製した。Comparative Example 2 Same as Example 1 except that 2 parts of elastic non-adhesive hollow thermoplastic polymer spheres [Expansel 551DE manufactured by Nippon Fluorite Co., Ltd.] were used in place of the silicone rubber particles. Then, a photopolymerizable adhesive composition was prepared, and an adhesive tape was prepared in the same manner as in Example 1 using this composition.
【0045】比較例3 シリコ―ンゴム粒子に代えて、架橋ポリスチレン球状マ
イクロビ―ズ〔住友化学工業(株)製のフアインパ―ル
PB3011E〕15部を用いた以外は、実施例1と同
様にして光重合性接着剤組成物を調製し、この組成物を
用いて実施例1と同様にして接着テ―プを作製した。Comparative Example 3 The same procedure as in Example 1 was repeated except that 15 parts of crosslinked polystyrene spherical microbeads [Fair Impal PB3011E manufactured by Sumitomo Chemical Co., Ltd.] was used in place of the silicone rubber particles. A polymerizable adhesive composition was prepared, and an adhesive tape was produced in the same manner as in Example 1 using this composition.
【0046】参考例1 2−エチルヘキシルアクリレ―ト90部、アクリル酸1
0部、2・2´−アゾビスイソブチロニトリル0.4
部、酢酸エチル250部を、4つ口フラスコに投入し、
窒素雰囲気下60℃で10時間重合して、重合体溶液を
得た。この重合体溶液に、ポリマ―100部に対して、
平均粒径が3μmの球状のシリコ―ンゴム粒子〔東レ・
ダウコ―ニング・シリコ―ン(株)製のトレフイルE−
500〕15部、3官能のイソシアネ―ト化合物2部を
添加して、感圧性接着剤溶液を調製した。Reference Example 1 2-Ethylhexyl acrylate 90 parts, acrylic acid 1
0 part, 2.2'-azobisisobutyronitrile 0.4
Parts, 250 parts of ethyl acetate are charged into a four-necked flask,
Polymerization was carried out at 60 ° C. for 10 hours in a nitrogen atmosphere to obtain a polymer solution. To this polymer solution, for 100 parts of polymer,
Spherical silicone rubber particles with an average particle size of 3 μm [Toray
Trefoil E- manufactured by Dow Corning Silicone Co., Ltd.
500] 15 parts of 2 parts of trifunctional isocyanate compound was added to prepare a pressure sensitive adhesive solution.
【0047】つぎに、この接着剤溶液を、厚さが25μ
mのポリエチレンテレフタレ―トフイルム上に、乾燥後
の厚さが400μmとなるように塗布し、40℃で5分
間乾燥後、100℃で5分間乾燥して、接着テ―プを得
た。Next, this adhesive solution was added to a thickness of 25 μm.
m of polyethylene terephthalate film so that the thickness after drying was 400 μm, dried at 40 ° C. for 5 minutes and then at 100 ° C. for 5 minutes to obtain an adhesive tape.
【0048】上記の実施例1〜4、比較例1〜3および
参考例1の各接着テ―プにつき、その接着特性を調べた
結果は、つぎの表1に示されるとおりであつた。The adhesive properties of the adhesive tapes of Examples 1 to 4, Comparative Examples 1 to 3 and Reference Example 1 were examined, and the results are shown in Table 1 below.
【0049】[0049]
【表1】 [Table 1]
【0050】上記の表1の結果より、本発明の実施例1
〜4の接着テ―プは、比較例および参考例の接着テ―プ
に比べ、低温から高温までの接着特性にすぐれ、しかも
低温での耐衝撃性にすぐれたものであることがわかる。From the results of Table 1 above, Example 1 of the present invention
It can be seen that the adhesive tapes Nos. 4 to 4 have excellent adhesive properties from low temperature to high temperature and excellent impact resistance at low temperature, as compared with the adhesive tapes of Comparative Example and Reference Example.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 吉川 孝雄 大阪府茨木市下穂積1丁目1番2号 日東 電工株式会社内 ─────────────────────────────────────────────────── ─── Continued Front Page (72) Inventor Takao Yoshikawa 1-2-1, Shimohozumi, Ibaraki City, Osaka Prefecture Nitto Denko Corporation
Claims (5)
ルキル(メタ)アクリレ―ト単量体を主成分とする主単
量体70〜99重量%と、極性基含有の共重合性単量体
30〜1重量%とからなる単量体混合物100重量部 b)シリコ―ンゴム粒子2〜60重量部 c)光重合開始剤0.01〜5重量部 を必須成分として含有することを特徴とする光重合性接
着剤組成物。1. The following a to c three components; a) A main monomer 70 to 99 containing an alkyl (meth) acrylate monomer whose alkyl group has an average of 1 to 14 carbon atoms as a main component. 100 parts by weight of a monomer mixture composed of 30% by weight of a polar group-containing copolymerizable monomer b) 2 to 60 parts by weight of silicone rubber particles c) 0.01 to 0.01 of a photopolymerization initiator A photopolymerizable adhesive composition comprising 5 parts by weight as an essential component.
を光重合して、感圧接着性および凝集力を付与してなる
感圧性接着剤。2. A pressure-sensitive adhesive obtained by photopolymerizing the photopolymerizable adhesive composition according to claim 1 to impart pressure-sensitive adhesiveness and cohesive force.
載の感圧性接着剤の層が設けられてなる接着シ―ト類。3. An adhesive sheet comprising a substrate and a layer of the pressure-sensitive adhesive according to claim 2 provided on one side or both sides of the substrate.
ゴム粒子が、その層の厚さよりも小さい平均粒径を有す
る請求項3に記載の接着シ―ト類。4. The adhesive sheet according to claim 3, wherein the silicone rubber particles contained in the pressure-sensitive adhesive layer have an average particle size smaller than the thickness of the layer.
り、そのうちの少なくとも1層が請求項2に記載の感圧
性接着剤の層からなる接着シ―ト類。5. An adhesive sheet in which the pressure-sensitive adhesive layer has a multi-layer structure, at least one layer of which is formed of the pressure-sensitive adhesive layer according to claim 2.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP03334214A JP3091783B2 (en) | 1991-11-21 | 1991-11-21 | Photopolymerizable adhesive composition, pressure-sensitive adhesive using the same, and adhesive sheet |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP03334214A JP3091783B2 (en) | 1991-11-21 | 1991-11-21 | Photopolymerizable adhesive composition, pressure-sensitive adhesive using the same, and adhesive sheet |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH05140510A true JPH05140510A (en) | 1993-06-08 |
JP3091783B2 JP3091783B2 (en) | 2000-09-25 |
Family
ID=18274823
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP03334214A Expired - Lifetime JP3091783B2 (en) | 1991-11-21 | 1991-11-21 | Photopolymerizable adhesive composition, pressure-sensitive adhesive using the same, and adhesive sheet |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP3091783B2 (en) |
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WO2012150682A1 (en) * | 2011-05-02 | 2012-11-08 | 日東電工株式会社 | Adhesive, adhesive layer, and adhesive sheet |
JP2012246477A (en) * | 2011-05-02 | 2012-12-13 | Nitto Denko Corp | Adhesive, adhesive layer, and adhesive sheet |
US10308844B2 (en) | 2011-05-02 | 2019-06-04 | Nitto Denko Corporation | Pressure-sensitive adhesive, pressure-sensitive adhesive layer, and pressure-sensitive adhesive sheet |
JP2017082228A (en) * | 2012-07-31 | 2017-05-18 | 日東電工株式会社 | Radiation-curable adhesive, radiation-curable adhesive layer, radiation-curable adhesive sheet and laminate |
JP2018507276A (en) * | 2014-12-23 | 2018-03-15 | サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. | Adhesive composition, adhesive film formed therefrom and display member comprising the same |
JP2021095580A (en) * | 2019-06-10 | 2021-06-24 | 味の素株式会社 | Insulation resin material |
CN110951447A (en) * | 2019-11-14 | 2020-04-03 | 烟台德邦科技有限公司 | Free radical, moisture and UV triple curing sealant and preparation method thereof |
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