JP6044689B2 - Method for producing double-sided PSA sheet and double-sided PSA sheet - Google Patents
Method for producing double-sided PSA sheet and double-sided PSA sheet Download PDFInfo
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Description
本発明は、両面粘着シートの製造方法及び両面粘着シートに関する。 The present invention relates to a method for producing a double-sided PSA sheet and a double-sided PSA sheet.
現在、液晶やタッチパネル等の画面は、液晶などの画像表示部を外部からの衝撃から保護する観点から一般的にＬＣＤと前面板に空間を設けている。しかし、屈折率の違い等により、反射光や散乱光で画質が低下する問題があった。そこで、これらの空間を両面粘着シートにて充填することが提案されており、これらの粘着シートは、一般に有機溶剤で溶液重合して得られる溶剤系の溶液、水系で乳化重合して得られるエマルジョン、または、光重合樹脂組成物等を硬化して用いられる。これにより、反射光や散乱光を防止し、画質のコントラスト上昇や反射光を改善することができる（例えば、特許文献１参照）。 Currently, a screen such as a liquid crystal or a touch panel generally has a space in the LCD and the front plate from the viewpoint of protecting an image display unit such as a liquid crystal from an external impact. However, there is a problem that the image quality deteriorates due to reflected light or scattered light due to a difference in refractive index. Therefore, it has been proposed to fill these spaces with a double-sided PSA sheet. These PSA sheets are generally a solvent-based solution obtained by solution polymerization with an organic solvent, or an emulsion obtained by emulsion polymerization in an aqueous system. Alternatively, it is used by curing a photopolymerization resin composition or the like. Thereby, reflected light and scattered light can be prevented, and the contrast of image quality can be increased and reflected light can be improved (see, for example, Patent Document 1).
しかしながら、これらの両面粘着シートは単層構造であり、ＬＣＤ（ガラス）と前面板（ガラス、アクリル板、ポリカーボネート）の被着体が異なると、被着体毎に粘着力が変化するため、粘着力が小さい方から剥れが発生する問題があった。また、粘着力に優れる材料は、衝撃吸収力が低いなどの問題があった。 However, these double-sided pressure-sensitive adhesive sheets have a single-layer structure, and if the adherends of LCD (glass) and front plate (glass, acrylic plate, polycarbonate) are different, the adhesive force changes for each adherend. There was a problem that peeling occurred from the smaller force. In addition, materials having excellent adhesive strength have problems such as low impact absorption.
これらの問題を解決するために、異なる物性を有する樹脂組成物を用いて多層膜を形成し、被着体と接する最外層の樹脂層を被着体に合わせ選定する方法が提案されており、これにより異なる被着体に対しても剥れのない粘着シートを作製することができ、個別に作製した複数の粘着シートを貼り合わせる方法（ラミネート方式による多層化）などが提案されている。 In order to solve these problems, a method of forming a multilayer film using resin compositions having different physical properties and selecting an outermost resin layer in contact with the adherend according to the adherend has been proposed, As a result, a pressure-sensitive adhesive sheet that does not peel off even on different adherends can be produced, and a method of laminating a plurality of individually produced pressure-sensitive adhesive sheets (multi-layering by a laminate method) has been proposed.
複数層構造の粘着シートの製造方法では、溶剤系の溶液およびエマルジョンは乾燥により硬化するが、高温での乾燥が必要であるためエネルギー効率が悪く、また大気汚染防止のための大規模な溶剤回収装置が必要である。 In the method for producing a multi-layered PSA sheet, solvent-based solutions and emulsions are cured by drying, but they are not energy efficient because they need to be dried at high temperatures, and large-scale solvent recovery is performed to prevent air pollution. Equipment is needed.
一方、光重合樹脂組成物では、溶剤系の溶液やエマルジョンを用いる場合と比較して紫外線などの電子線にて硬化するため、硬化時間が短く、エネルギー効率が高いことや膜厚の調整なども容易であり、溶剤を含有する必要が無いため、安全面や環境面においても優れているが、光重合樹脂は、硬化時に酸素による重合阻害が起こる問題があり、塗工面を光透過性カバーフィルムで覆う、または窒素などの不活性雰囲気中で照射を行う必要があった。光透過性カバーフィルムで覆う場合、光重合樹脂ラミネート方式による多層化では、層毎に光透過性カバーフィルム貼合と剥離作業が必要となる。また、工程数増加による異物混入や歩留悪化の問題が発生した。 On the other hand, the photopolymerization resin composition is cured with an electron beam such as ultraviolet rays as compared with the case of using a solvent-based solution or emulsion, so that the curing time is short, the energy efficiency is high, and the film thickness is adjusted. Although it is easy and does not need to contain a solvent, it is excellent in terms of safety and environment. However, the photopolymerization resin has a problem in that polymerization is inhibited by oxygen at the time of curing, and the coated surface has a light-transmitting cover film. Or irradiation in an inert atmosphere such as nitrogen. In the case of covering with a light-transmitting cover film, multilayering by a photopolymerization resin laminate method requires light-transmitting cover film bonding and peeling work for each layer. In addition, foreign matter contamination due to an increase in the number of processes and a problem of yield deterioration occurred.
本発明の目的は、異なる物性を有する光重合樹脂を多層化する両面粘着シートを光透過性カバーフィルムのロスなく、かつ高歩留で製造する方法を提供することである。 An object of the present invention is to provide a method for producing a double-sided pressure-sensitive adhesive sheet in which photopolymerization resins having different physical properties are multilayered without loss of a light-transmitting cover film and at a high yield.
上記目的を達成するため、鋭意検討した結果、複数の樹脂組成物を同時に塗工する、同時多層塗工を実施し、その後直ちにカバーフィルムをラミネートし、ＵＶ硬化を行うことで達成できることを見出した。
本発明は、以下に関する。
１． 物性が異なる複数の樹脂層を有する両面粘着シートの製造方法であって、（１）塗工対象面に複数の光重合樹脂組成物を同時に塗工し、複数の樹脂層を形成する工程（以下、同時多層塗工と表す）と、（２）形成した樹脂層に光透過性フィルムをラミネートする工程と、（３）ラミネート後に紫外線または電子線を照射し、樹脂層を硬化させる工程とを有する両面粘着シートの製造方法。
２． 光重合樹脂組成物が溶剤を含有しない樹脂組成物である前記の両面粘着シートの製造方法。
３． 工程（１）において、複数の樹脂層の各層の膜厚がそれぞれ１５〜２０００μｍであり、樹脂層の総厚みが３０〜３０００μｍである前記の両面粘着シートの製造方法。
４． 前記の両面粘着シートの製造方法により製造してなる両面粘着シート。
５． 複数の樹脂層の最外層の２つの層の粘着力が異なる前記の両面粘着シート。
As a result of intensive studies to achieve the above object, it has been found that a plurality of resin compositions can be applied simultaneously, simultaneous multilayer coating is performed, a cover film is immediately laminated, and then UV curing is performed. .
The present invention relates to the following.
1. A method for producing a double-sided pressure-sensitive adhesive sheet having a plurality of resin layers having different physical properties, wherein (1) a step of simultaneously applying a plurality of photopolymerized resin compositions on a surface to be coated to form a plurality of resin layers (hereinafter referred to as “a plurality of resin layers”) , Which is expressed as simultaneous multilayer coating), (2) a step of laminating a light transmissive film on the formed resin layer, and (3) a step of curing the resin layer by irradiating ultraviolet rays or electron beams after lamination. A method for producing a double-sided PSA sheet.
2. The manufacturing method of the said double-sided adhesive sheet whose photopolymerization resin composition is a resin composition which does not contain a solvent.
3. In the step (1), the thickness of each layer of the plurality of resin layers is 15 to 2000 μm, and the total thickness of the resin layers is 30 to 3000 μm.
4). A double-sided pressure-sensitive adhesive sheet produced by the above-described method for producing a double-sided pressure-sensitive adhesive sheet.
5. The double-sided pressure-sensitive adhesive sheet, wherein the two outermost layers of the plurality of resin layers have different adhesive forces.
本発明により、多層化時の光透過カバーフィルムの材料ロスおよび工程数を削減することで、高歩留で異なる物性を有する光重合樹脂の多層化を行うことが出来る。また、懸念される層間の樹脂混合はなく、両面（多層）粘着シートは、光学特性、粘着力ともにラミネート方式と同等の特性を得ることができる。 According to the present invention, by reducing the material loss and the number of steps of the light-transmitting cover film at the time of multilayering, it is possible to multilayer the photopolymerization resin having different physical properties with high yield. Moreover, there is no resin mixing between layers concerned, and the double-sided (multi-layer) pressure-sensitive adhesive sheet can obtain characteristics equivalent to those of the laminate system in both optical characteristics and adhesive strength.
本発明は、両面粘着シートの製造方法であって、同時多層塗工により、異なる物性を有する樹脂層を複数形成し、その後、ＵＶ等の光照射により樹脂を硬化させる工程を有するものである。 The present invention is a method for producing a double-sided pressure-sensitive adhesive sheet, and includes a step of forming a plurality of resin layers having different physical properties by simultaneous multilayer coating and then curing the resin by irradiation with light such as UV.
本発明において、両面粘着シートは、異なる物性を有する複数の樹脂層を有する。複数とは、少なくとも２層以上であり、２〜５層が好ましく、より好ましくは２〜３層である。異なる物性とは、粘着力、衝撃吸収性、オートクレーブ消泡性等が挙げられる。例えば、樹脂層を２層とし、粘着シート両面の被着体が異なる場合に被着体にあわせて粘着力を変化させたり、樹脂層を３層とし、外層部に被着体と粘着性の高い樹脂層を設け、内部に衝撃吸収性の高い樹脂層を設けたり、樹脂を３層とし、外層部にオートクレーブ処理により気泡が消泡しやすい樹脂層を設けたりし、用途に合わせて樹脂層を組み合わせることが好ましい。
また、本発明の両面粘着シートの複数の樹脂層の最外層の２つの層の粘着力が異なることが好ましい。最外層の２つの層の粘着力の差は、通常１〜１５Ｎ／ｃｍ、好ましくは４〜１０Ｎ／ｃｍである。
In the present invention, the double-sided PSA sheet has a plurality of resin layers having different physical properties. The term “plurality” refers to at least two layers, preferably 2 to 5 layers, and more preferably 2 to 3 layers. Examples of different physical properties include adhesive strength, impact absorption, and autoclave defoaming. For example, if the resin layer has two layers and the adherends on both sides of the pressure-sensitive adhesive sheet are different, the adhesive force is changed according to the adherend, or the resin layer has three layers, and the adherend and adhesive properties are formed on the outer layer portion. A high resin layer is provided, a resin layer with high shock absorption is provided inside, and three resin layers are provided, and a resin layer in which bubbles are easily removed by autoclaving is provided on the outer layer portion. Are preferably combined.
Moreover, it is preferable that the adhesive force of two outermost layers of the several resin layer of the double-sided adhesive sheet of this invention differs. The difference in adhesive strength between the two outermost layers is usually 1 to 15 N / cm, preferably 4 to 10 N / cm.
なお、異なる物性を有する樹脂層は、光重合樹脂組成物を積層することにより形成される。また、光重合樹脂組成物の組成を調整することにより、樹脂層の物性を変化させる。 光重合樹脂組成物（光学樹脂組成物）としては、粘着シートとして使用した際に適切な粘着力があり、光学特性に問題が無いものであれば、特に限定はないが、アクリル酸系誘導体を含有することが好ましい。例えば、粘着力を向上させるためには、アクリル酸系誘導体が、アルキル基の炭素数が４〜１８であるアルキルアクリレートと、水酸基、モルホリル基等の極性基を含有するアクリレートの混合物であることが好ましく、衝撃吸収性を向上させるためには、重量平均分子量１００，０００以上のアクリル酸系誘導体ポリマーを含有することが好ましい。また、塗工しやすさの観点からは、硬化前の樹脂組成物の粘度は、７５０〜１００００ｃｐであることが好ましい。また、硬化時などに溶剤の揮発を防ぐため、樹脂組成物には溶剤を含まないことが好ましい。 In addition, the resin layer which has a different physical property is formed by laminating | stacking a photopolymerization resin composition. Moreover, the physical property of a resin layer is changed by adjusting the composition of a photopolymerization resin composition. The photopolymerization resin composition (optical resin composition) is not particularly limited as long as it has an appropriate adhesive force when used as an adhesive sheet and has no problem in optical properties. It is preferable to contain. For example, in order to improve adhesion, the acrylic acid derivative is a mixture of an alkyl acrylate having 4 to 18 carbon atoms in an alkyl group and an acrylate containing a polar group such as a hydroxyl group or a morpholyl group. Preferably, an acrylic acid derivative polymer having a weight average molecular weight of 100,000 or more is preferably contained in order to improve impact absorption. Moreover, from the viewpoint of easy coating, the viscosity of the resin composition before curing is preferably 750 to 10,000 cp. Further, in order to prevent the solvent from evaporating at the time of curing or the like, it is preferable that the resin composition does not contain a solvent.
次に同時多層塗工工程について説明する。同時多層塗工工程とは、物性の異なる硬化前の光重合樹脂組成物を複数同時に塗工する工程である。多層化する方法としては、同時多層塗工の他に、各層をそれぞれ個別に塗工及び硬化して作製した後に貼り合わせるラミネート方式や、塗工及び硬化した層の上に新たに別の層を塗工し硬化する事を繰り返す逐次多層塗工があるが、これらは同時多層塗工と比較して、硬化の際に光透過性カバーフィルムで覆う工程が複数回必要となり、よって本発明の目的を達成するためには、同時多層塗工を行うことが必要となる。なお、溶剤系の溶液やエマルジョンなど乾燥により硬化する場合は、硬化のためにカバーフィルムで覆う必要がないため、ラミネート方式や逐次多層塗工も光重合樹脂組成物と比較して容易であり、乾燥条件の設定の容易性を考慮すると、複数の樹脂層の乾燥条件を考慮する必要のある同時多層塗工よりも好ましい。 Next, the simultaneous multilayer coating process will be described. The simultaneous multilayer coating process is a process in which a plurality of prepolymerized photopolymerization resin compositions having different physical properties are applied simultaneously. In addition to simultaneous multi-layer coating, multiple layers can be applied by laminating each layer individually after being individually coated and cured, or by adding another layer on the coated and cured layer. There are sequential multilayer coating that repeats coating and curing, but these require multiple steps of covering with a light-transmitting cover film at the time of curing compared to simultaneous multilayer coating, and therefore the object of the present invention In order to achieve this, simultaneous multilayer coating is required. In addition, when cured by drying, such as solvent-based solutions and emulsions, since it is not necessary to cover with a cover film for curing, laminating methods and sequential multilayer coating are also easier compared to photopolymerized resin compositions, Considering the ease of setting the drying conditions, it is preferable to simultaneous multilayer coating in which the drying conditions of a plurality of resin layers need to be considered.
同時多層塗工について図面に基づいて説明する。但し、本発明の多層工程はこの方法に限定されるものではない。同時多層塗工は、図１に示す断面構造の多層塗工コーターを用いて行うことが出来る。図の１は、塗工基材であり、その上に多層コーター２が設置される。異なる特性の光硬化性樹脂組成物はそれぞれの樹脂セット位置３、４、５にセットされ、多層コーター２を図２のように動かすことで、光硬化性樹脂がバー６、７、８により目標厚みに整えられて、多層構造を形成する。
Simultaneous multilayer coating will be described with reference to the drawings. However, the multilayer process of the present invention is not limited to this method. Simultaneous multilayer coating can be performed using a multilayer coating coater having a cross-sectional structure shown in FIG. In the figure,
バーの高さは０〜２０００μｍまで可変することができることが好ましい。これにより、合せて各層の厚みも０〜２０００μｍまで可変することができる。安定した樹脂層を形成するためには、各樹脂層の厚みが１５μｍ以上であることが好ましく、５０μｍ以上であることが更に好ましく、通常使用する粘着シートの厚みを考慮すると各樹脂層の厚みは２０００μｍ以下であることが好ましく、更に５００μｍ以下であることがより好ましい。また、各樹脂層の厚みを合計した樹脂層の総厚みは、３０〜３０００μｍであることが好ましく、１００〜１０００μｍであることがより好ましい。 The height of the bar is preferably variable from 0 to 2000 μm. Thereby, the thickness of each layer can also be varied from 0 to 2000 μm. In order to form a stable resin layer, the thickness of each resin layer is preferably 15 μm or more, more preferably 50 μm or more, and considering the thickness of the pressure-sensitive adhesive sheet that is usually used, the thickness of each resin layer is It is preferably 2000 μm or less, and more preferably 500 μm or less. Moreover, it is preferable that it is 30-3000 micrometers, and, as for the total thickness of the resin layer which totaled the thickness of each resin layer, it is more preferable that it is 100-1000 micrometers.
上記構造の塗工コーターを用いた場合、樹脂組成物の粘度は、３００ｃｐ〜２００００ｃｐまで対応することができる。 When the coating coater having the above structure is used, the viscosity of the resin composition can correspond to 300 cp to 20000 cp.
次に、形成した樹脂層に光透過性フィルムをラミネートする工程について説明する。この工程は、塗工した光重合樹脂組成物を硬化する際に酸素による重合阻害を防ぐために、通常行われている工程であり、樹脂層を覆うように光透過性フィルムをラミネート出来れば、特に問題はないが、エネルギー効率の観点から高透過率のフィルムが好ましい。 Next, the process of laminating a light transmissive film on the formed resin layer will be described. This step is a commonly performed step to prevent polymerization inhibition due to oxygen when curing the coated photopolymerization resin composition, especially if a light transmissive film can be laminated to cover the resin layer. Although there is no problem, a film having a high transmittance is preferable from the viewpoint of energy efficiency.
次に、樹脂を硬化させる工程について説明する。樹脂は、紫外線や電子線を照射することで、架橋反応が開始し、硬化する。通常の光重合樹脂組成物の場合、照射量５００ｍＪ／ｃｍ２以上で樹脂を硬化させることができ、公知の方法で行うことができる。 Next, the process of curing the resin will be described. When the resin is irradiated with ultraviolet rays or an electron beam, the crosslinking reaction starts and the resin is cured. In the case of a normal photopolymerization resin composition, the resin can be cured at an irradiation amount of 500 mJ / cm 2 or more, and can be performed by a known method.
上記方法により、製造された粘着シートは、異なる物性を有する樹脂層を複数有することで、各層の特性を組み合わせることができ、また、各層を同時に塗工及び硬化するため、各層の密着性が高い。 The pressure-sensitive adhesive sheet produced by the above method can combine the properties of each layer by having a plurality of resin layers having different physical properties, and each layer is coated and cured simultaneously, so that the adhesion of each layer is high. .
以下、２種類の光重合樹脂組成物（無溶剤）を用いて各層１５０μｍ、総厚３００μｍの厚みで塗工した場合について説明する。なお、厚み、樹脂種類、層形成樹脂数に関しては、これに限定されるものではない。
（両面粘着シートの製造）
塗工に用いた樹脂は、アクリル系光硬化性樹脂２種類（Ａ樹脂・Ｂ樹脂）であり、この樹脂を図１に示す多層コーターにセットした（Ａ樹脂を樹脂セット位置３に、Ｂ樹脂を樹脂セット位置４にセットした）。多層コーターのバーの高さを樹脂厚みが各層それぞれ１５０μｍになるように調整し、同時に２層を形成した。２層形成後直ちに光透過性カバーフィルムをラミネートし、その後紫外線を２０００ｍＪ／ｃｍ２照射し、硬化した。
Hereinafter, the case where it coats by the thickness of each layer 150 micrometers and the total thickness of 300 micrometers using two types of photopolymerization resin compositions (solvent-free) is demonstrated. Note that the thickness, the resin type, and the number of layer forming resins are not limited thereto.
(Manufacture of double-sided PSA sheet)
The resin used for coating was two types of acrylic photo-curing resins (A resin and B resin), and this resin was set on the multilayer coater shown in FIG. Was set at resin setting position 4). The height of the bar of the multilayer coater was adjusted so that the resin thickness was 150 μm for each layer, and two layers were formed simultaneously. Immediately after the formation of the two layers, a light-transmitting cover film was laminated, and then irradiated with 2000 mJ / cm 2 of ultraviolet rays to be cured.
（Ａ樹脂）
アクリル酸系誘導体ポリマー１ ２４．９０ｇ、
２−エチルヘキシルアクリレート ２７．９０ｇ、
２−ヒドロキシエチルアクリレート １１．９０ｇ、
ポリウレタンアクリレート１ ３４．８０ｇ、
１−ヒドロキシ−シクロヘキシル−フェニル−ケトン（光重合開始剤） ０．５０ｇ
を加え、攪拌混合して、光重合樹脂組成物（光学用樹脂組成物）を調製した。
(A resin)
24.90 g of acrylic acid
2-ethylhexyl acrylate 27.90 g,
11.90 g of 2-hydroxyethyl acrylate,
34.80 g of
1-hydroxy-cyclohexyl-phenyl-ketone (photopolymerization initiator) 0.50 g
Was added and stirred and mixed to prepare a photopolymerization resin composition (optical resin composition).
（Ｂ樹脂）
アクリル酸系誘導体ポリマー１ ２８．６０ｇ、
２−エチルヘキシルアクリレート ４０．５０ｇ、
アクリロイルモルホリン １７．４０ｇ、
ポリウレタンアクリレート２ １３．００ｇ、
１−ヒドロキシ−シクロヘキシル−フェニル−ケトン（光重合開始剤） ０．５０ｇ
を加え、攪拌混合して、光重合樹脂組成物（光学用樹脂組成物）を調製した。
(B resin)
28.60 g of acrylic acid
40.50 g of 2-ethylhexyl acrylate,
Acryloylmorpholine 17.40 g,
1-hydroxy-cyclohexyl-phenyl-ketone (photopolymerization initiator) 0.50 g
Was added and stirred and mixed to prepare a photopolymerization resin composition (optical resin composition).
（アクリル酸系誘導体ポリマー１の合成）
冷却管、温度計、撹拌装置、滴下漏斗及び窒素注入管の付いた反応容器に初期モノマーとして、２−エチルヘキシルアクリレート８４．０ｇと２−ヒドロキシエチルアクリレート３６．０ｇ並びにメチルイソブチルケトン１５０．０ｇをとり１００ｍｌ／ｍｉｎの風量で窒素置換しながら、１５分間で常温（２５℃）から７０℃まで加熱した。その後、この温度に保ちながら、追加モノマーとして、２−エチルヘキシルアクリレート２１．０ｇと２−ヒドロキシエチルアクリレート９．０ｇを使用し、これらにラウロイルパーオキシド０．６ｇを溶解した溶液を準備し、この溶液を６０分間かけて滴下し、滴下終了後さらに２時間反応させた。続いて、メチルイソブチルケトンを溜去することにより２−エチルヘキシルアクリレートと２−ヒドロキシエチルアクリレートのコポリマー（重量平均分子量２５０，０００）を得た。
(Synthesis of acrylic acid derivative polymer 1)
Into a reaction vessel equipped with a condenser, thermometer, stirrer, dropping funnel and nitrogen injection tube, 84.0 g of 2-ethylhexyl acrylate, 36.0 g of 2-hydroxyethyl acrylate and 150.0 g of methyl isobutyl ketone are taken as initial monomers. Heating was performed from room temperature (25 ° C.) to 70 ° C. in 15 minutes while purging with nitrogen at an air volume of 100 ml / min. Thereafter, while maintaining this temperature, 21.0 g of 2-ethylhexyl acrylate and 9.0 g of 2-hydroxyethyl acrylate were used as additional monomers, and a solution in which 0.6 g of lauroyl peroxide was dissolved therein was prepared. Was added dropwise over 60 minutes, and the reaction was further continued for 2 hours after the completion of the dropwise addition. Subsequently, methyl isobutyl ketone was distilled off to obtain a copolymer of 2-ethylhexyl acrylate and 2-hydroxyethyl acrylate (weight average molecular weight 250,000).
（ポリウレタンアクリレート１の合成）
冷却管、温度計、攪拌装置、滴下漏斗及び空気注入管のついた反応容器にポリプロピレングリコール（分子量２，０００）２８５．３ｇ、ラクトン変性ヒドロキシエチルアクリレート２４．５ｇ、重合禁止剤としてｐ−メトキシフェノール０．１３ｇ、触媒としてジブチル錫ジラウレート０．５ｇをとり、空気を流しながら７５℃に昇温後、７０〜７５℃で攪拌しつつイソホロンジイソシアネート３９．６ｇを２時間かけて均一滴下し、反応を行った。滴下終了後、約５時間反応させたところで、さらに、ラクトン変性ヒドロキシエチルアクリレート２４．５ｇを追加し、約１時間反応させた。ＩＲ測定の結果、イソシアネートが消失したことを確認して反応を終了し、ポリプロピレングリコールとイソホロンジイソシアネートを繰り返し単位として有し、両末端に重合性不飽和結合を有するポリウレタンアクリレート（重量平均分子量２０，０００）を得た。
(Synthesis of polyurethane acrylate 1)
285.3 g of polypropylene glycol (molecular weight 2,000), 24.5 g of lactone-modified hydroxyethyl acrylate, p-methoxyphenol as a polymerization inhibitor in a reaction vessel equipped with a cooling tube, thermometer, stirring device, dropping funnel and air injection tube Take 0.13 g and 0.5 g of dibutyltin dilaurate as a catalyst, raise the temperature to 75 ° C. while flowing air, then uniformly drop 39.6 g of isophorone diisocyanate over 2 hours while stirring at 70 to 75 ° C. went. When the reaction was completed for about 5 hours after the completion of the dropwise addition, 24.5 g of lactone-modified hydroxyethyl acrylate was further added, and the reaction was performed for about 1 hour. As a result of IR measurement, it was confirmed that the isocyanate had disappeared, and the reaction was terminated. Polyurethane acrylate having a repeating unit of polypropylene glycol and isophorone diisocyanate and having a polymerizable unsaturated bond at both ends (weight average molecular weight 20,000) )
（ポリウレタンアクリレート２の合成）
冷却管、温度計、攪拌装置、滴下漏斗及び空気注入管のついた反応容器にポリプロピレングリコール（分子量２，０００）２８５．３ｇ、２−エチルヘキシルアクリレート１００．０ｇ、重合禁止剤としてｐ−メトキシフェノール０．１３ｇ、触媒としてジブチル錫ジラウレート０．５ｇをとり、空気を流しながら７５℃に昇温後、７０〜７５℃で攪拌しつつイソホロンジイソシアネート３９．６ｇを２時間かけて均一滴下し、反応を行った。滴下終了後、約５時間反応させたところで、さらに、ラクトン変性ヒドロキシエチルアクリレート２４．５ｇを追加し、約１時間反応させた。ＩＲ測定の結果、イソシアネートが消失したことを確認して反応を終了し、ポリプロピレングリコールとイソホロンジイソシアネートを繰り返し単位として有し、両末端に重合性不飽和結合を有するポリウレタンアクリレート（重量平均分子量３２，０００）を得た。
(Synthesis of polyurethane acrylate 2)
In a reaction vessel equipped with a cooling tube, a thermometer, a stirring device, a dropping funnel and an air injection tube, 285.3 g of polypropylene glycol (molecular weight 2,000), 100.0 g of 2-ethylhexyl acrylate, and p-methoxyphenol 0 as a polymerization inhibitor .13 g, 0.5 g of dibutyltin dilaurate as a catalyst, heated to 75 ° C. while flowing air, and then 39.6 g of isophorone diisocyanate was added dropwise uniformly over 2 hours while stirring at 70 to 75 ° C. to carry out the reaction. It was. When the reaction was completed for about 5 hours after the completion of the dropwise addition, 24.5 g of lactone-modified hydroxyethyl acrylate was further added, and the reaction was performed for about 1 hour. As a result of IR measurement, it was confirmed that the isocyanate had disappeared, and the reaction was terminated. Polyurethane acrylate having a repeating unit of polypropylene glycol and isophorone diisocyanate and having a polymerizable unsaturated bond at both ends (weight average molecular weight 32,000) )
実施例１
上記（両面粘着シートの製造方法）にて２層の粘着シートを作製した。使用した光透過性カバーフィルムは２枚であり、塗工開始から硬化完了までの時間は、約２分であり、効率よく作製することができた。
Example 1
A two-layer pressure-sensitive adhesive sheet was produced by the above-described method (manufacturing method of the double-sided pressure-sensitive adhesive sheet). Two light-transmitting cover films were used, and the time from the start of coating to the completion of curing was about 2 minutes, and could be produced efficiently.
実施例２
上記（両面粘着シートの製造方法）において、Ａ樹脂に、色素を添加し着色して、２層の状態を確認した。Ａ樹脂層、Ｂ樹脂層の２層の間にＡ樹脂・Ｂ樹脂混合層が１０μｍ形成されたが、その他の部分は樹脂が混合することはなく、目的の層に分離していることを確認できた。
Example 2
In the above (manufacturing method of a double-sided pressure-sensitive adhesive sheet), a pigment was added to the A resin and colored to confirm the state of two layers. The A resin / B resin mixed layer was formed 10 μm between the two layers of the A resin layer and the B resin layer, but the other parts were not mixed with the resin, and it was confirmed that the target layer was separated. did it.
比較例１
Ａ樹脂、Ｂ樹脂を各々一方のみを樹脂セット位置３にセットして塗工した以外は、上記（両面粘着シートの製造方法）と同様にして、単層にて作製した。その後、Ａ樹脂の粘着シートとＢ樹脂の粘着シートをラミネートし、２層の粘着シートを作製した。使用した光透過性カバーフィルムは４枚であり、塗工開始から硬化完了までの時間は、約４分（２種類のシート作製合計時間）であり、更に２枚のシートをラミネートして２層のシートにする時間も必要となり、実施例１の方法と比較して２倍以上の時間を要した。
Comparative Example 1
A single layer was prepared in the same manner as described above (manufacturing method of the double-sided pressure-sensitive adhesive sheet) except that only one of the A resin and B resin was set at the
実施例１及び比較例１で作製した２層の粘着シートについて、光学特性、耐衝撃性、Ａ樹脂層およびＢ樹脂層の粘着力を測定した。結果を表１に示す。
（評価方法）
１）光学特性
分光測色計（ミノルタ製，ＣＭ−５０８ｄ）を用い，作製した２層の粘着シートの視感透過率（Ｙ）及び色調（ｘ，ｙ）を測定した。
粘着シートのヘーズ（Ｈｚ）は、曇り度計（日本電色工業（株）製ＮＤＨ２０００）を用いてヘイズを測定した（ＪＩＳ Ｋ ７１３６に準拠）。
なお、試験片は、透明エラストマの両面に高透明ＰＥＴ（東洋紡製コスモシャイン４１００−１００μｍ）を貼合した状態で測定した。
２）耐衝撃性
作製した２層の粘着シートの片面のフィルムを剥離し，高透明ＰＥＴ（東洋紡製，Ａ４１００：１００μｍ）の易接着面に貼合後，３０ｍｍ×３０ｍｍに切り出した。さらに，もう一方のフィルムを剥離し，厚さ９ｍｍの金属板にハンドローラーを用いて貼り合わせた。５０９．４ｇの鋼球（ＵＬ１９５０準拠）を１０ｃｍの高さから落下させ，ロードセル（昭和測器製，ＳＨ−１０ｋＮ）及びひずみ計測ユニット（キーエンス製，ＮＲ−ＳＴ０４）を用い，金属板に加わる応力を電圧に換算し，そのピーク電圧を測定した。
なお、Ａ樹脂層およびＢ樹脂層のどちらを金属板に張付けても結果に変化はなかった。
３）粘着力
作製した２層の粘着シートの粘着力を測定するため、測定しない樹脂層側のフィルムを剥離し，Ａ４１００の易接着面に貼合後，２５ｍｍ幅に切り出した。その後、粘着力を測定したい樹脂層側のフィルムを剥離し，厚さ３．０ｍｍのソーダガラスに１．５ｋｇのハンドローラーを用いて貼合した。その後３０分放置した後，引張試験機（オリエンテック製，ＴＲＣ−１２１０）を用いて，所定の温度環境下，引き剥がし角度１８０°，引き剥がし速度２００ｍｍ／ｍｉｎでピール強度（粘着力）を測定した。
For the two-layered adhesive sheet prepared in Example 1 and Comparative Example 1, the optical properties, impact resistance, and adhesiveness of the A resin layer and B resin layer were measured. The results are shown in Table 1.
(Evaluation method)
1) Optical characteristics Using a spectrocolorimeter (manufactured by Minolta, CM-508d), the luminous transmittance (Y) and the color tone (x, y) of the prepared two-layer adhesive sheet were measured.
The haze (Hz) of the adhesive sheet was measured using a haze meter (NDH2000 manufactured by Nippon Denshoku Industries Co., Ltd.) (based on JIS K 7136).
In addition, the test piece measured in the state which bonded highly transparent PET (Toyobo Cosmo Shine 4100-100 micrometers) on both surfaces of the transparent elastomer.
2) Impact resistance The film of one side of the produced two-layer adhesive sheet was peeled off and bonded to an easy-adhesion surface of highly transparent PET (Toyobo, A4100: 100 μm), and then cut out to 30 mm × 30 mm. Further, the other film was peeled off and bonded to a 9 mm thick metal plate using a hand roller. A 509.4 g steel ball (UL1950 compliant) is dropped from a height of 10 cm, and a stress applied to the metal plate using a load cell (SH-10kN, manufactured by Showa Sokki Co., Ltd.) and a strain measuring unit (manufactured by Keyence, NR-ST04) Was converted to voltage and the peak voltage was measured.
Note that there was no change in the result when either the A resin layer or the B resin layer was attached to the metal plate.
3) Adhesive strength In order to measure the adhesive strength of the prepared two-layer adhesive sheet, the film on the resin layer side that was not measured was peeled off, and bonded to the easy-adhesion surface of A4100, and then cut out to a width of 25 mm. Thereafter, the film on the resin layer side for which the adhesive strength was to be measured was peeled off and bonded to a 3.0 mm thick soda glass using a 1.5 kg hand roller. After leaving for 30 minutes, peel strength (adhesive strength) was measured at a peeling angle of 180 ° and a peeling speed of 200 mm / min using a tensile testing machine (Orientec, TRC-1210). did.
なお、光学特性については、視感透過率（Ｙ）、色調（ｘ，ｙ）はそれぞれ、Ｙが８０〜１００％、ｘが０．３０〜０．３２、ｙが０．３１〜０．３３の間に入ることが好ましく、実施例、比較例ともに範囲内であった。また、ヘーズ（Ｈｚ）は、粘着シートの濁りをしめす値であり、小さい方が好ましい。
表１に示すように、光学特性、耐衝撃性、Ａ樹脂層およびＢ樹脂層の粘着力ともに、実施例１の同時多層塗工方式は、比較例１のラミネート方式と比較して、ほぼ同等の結果が得られた。
As for the optical characteristics, the luminous transmittance (Y) and the color tone (x, y) are 80 to 100% for Y, 0.30 to 0.32 for x, and 0.31 to 0.33 for y. It was preferable to enter between, and both the examples and comparative examples were within the range. Moreover, haze (Hz) is a value which shows the cloudiness of an adhesive sheet, and the smaller one is preferable.
As shown in Table 1, the simultaneous multilayer coating method of Example 1 is almost the same as the laminate method of Comparative Example 1 in terms of optical properties, impact resistance, and adhesive strength of the A resin layer and B resin layer. Results were obtained.
１：塗工基材、２：多層コーター、３：１層目樹脂セット位置、４：２層目樹脂セット位置、５：３層目樹脂セット位置、６：１層目のバー、７：２層目のバー、８：３層目のバー
1: coating substrate, 2: multi-layer coater, 3: 1 layer resin setting position, 4: 2nd layer resin setting position, 5: 3rd layer resin setting position, 6: 1 layer bar, 7: 2 Layer Bar, 8:
Claims (8)
前記複数の光重合樹脂組成物の少なくとも一つが、モルホリル基を含有するアクリレートを含む、両面粘着シートの製造方法。 A method for producing a double-sided pressure-sensitive adhesive sheet having a plurality of resin layers having different physical properties, (1) a step of simultaneously applying a plurality of photopolymerization resin compositions on a surface to be coated, and forming a plurality of resin layers; (2) a step of laminating a light transmissive film formed resin layer was irradiated with ultraviolet light or an electron beam after (3) laminating, have a curing the resin layer,
The method for producing a double-sided pressure-sensitive adhesive sheet, wherein at least one of the plurality of photopolymerizable resin compositions contains an acrylate containing a morpholyl group .
二つの前記光重合樹脂組成物のうちの一方がアクリロイルモルホリンを含み、他方が２−ヒドロキシエチルアクリレートを含む、請求項１〜４のいずれか一項に記載の両面粘着シートの製造方法。The method for producing a double-sided pressure-sensitive adhesive sheet according to any one of claims 1 to 4, wherein one of the two photopolymerization resin compositions contains acryloylmorpholine and the other contains 2-hydroxyethyl acrylate.
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