JP2018024785A - Uv curable type resin composition - Google Patents

Uv curable type resin composition Download PDF

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JP2018024785A
JP2018024785A JP2016158145A JP2016158145A JP2018024785A JP 2018024785 A JP2018024785 A JP 2018024785A JP 2016158145 A JP2016158145 A JP 2016158145A JP 2016158145 A JP2016158145 A JP 2016158145A JP 2018024785 A JP2018024785 A JP 2018024785A
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resin composition
meth
component
mass
acrylate
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JP6502295B2 (en
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佐藤　信之
Nobuyuki Sato
信之 佐藤
裕美 福田
Hiromi Fukuda
裕美 福田
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Arisawa Mfg Co Ltd
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Arisawa Mfg Co Ltd
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Priority to JP2016158145A priority Critical patent/JP6502295B2/en
Priority to TW106123152A priority patent/TWI679262B/en
Priority to KR1020170089049A priority patent/KR102393003B1/en
Priority to CN201710576642.XA priority patent/CN107722916B/en
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Abstract

PROBLEM TO BE SOLVED: To provide a UV curable type resin composition which can easily peel LCD from an adherend even at normal temperature and rework the LCD, and can impart good adhesiveness, and to provide an adhesive sheet containing the same.SOLUTION: A UV curable type resin composition contains (A) a UV curable type prepolymer, (B) a UV curable type polyfunctional monomer, (C) a photopolymerization initiator and (D) a silane coupling agent, where the component (A) is urethane(meth)acrylate, and a content of the component (B) is 15-60 pts.mass, a content of the component (C) is 0.5 pts.mass or more and a content of the component (D) is 0.1-5 pts.mass with respect to 100 pts.mass of the component (A).SELECTED DRAWING: None

Description

本発明は、液晶ディスプレイ表示部に使用可能なＵＶ硬化型樹脂組成物及びそれを含む接着シートに関する。   The present invention relates to a UV curable resin composition that can be used in a liquid crystal display portion and an adhesive sheet containing the same.

現在、液晶ディスプレイ（ＬＣＤ）は、デジタル化された電子機器の普及に伴いごく一般的な表示装置となっており、液晶テレビやＰＣディスプレイ、携帯電話端末、携帯型ゲーム機、電卓、時計など、さまざまな機器の表示部として用いられている。特に、近年は、３Ｄ機能を付与することを目的として、ＬＣＤに、ガラスからなるパターニング位相差板を接着したものが存在する。
ここで、位相差板が接着されたＬＣＤは、使用後に回収され、ＬＣＤのみ再利用されることがある。例えば、位相差板をＬＣＤから剥がして、ＬＣＤをリワークすることが求められている。このとき、従来の方法では、ＬＣＤ全体を冷却して（換言すれば接着剤を冷却して）、ＬＣＤから位相差板を剥がす手法がとられていた。しかしながら、この方法では、冷却のための設備が必要であり、作業性も良いとは言えなかった。さらに、位相差板とＬＣＤが共に剛性を有しているため、剥がす際にどちらか一方が破損するという問題があった。すなわち、従来の接着シートは、ＬＣＤと位相差板を接着後、容易に引き剥がしてＬＣＤをリワークする事が困難であった。
このような問題点を解決するために、常温で、かつ被着体がガラスのように硬いものであっても容易に剥がすことができる接着シートが検討されている。例えば、特許文献１には、接着剤成分と、紫外線を照射することにより気体を発生する気体発生剤とを含有する透明接着フィルムが提案されている。また、特許文献２には、熱および化学線硬化型（光硬化型）接着剤組成物が提案されている。 At present, liquid crystal displays (LCDs) have become very common display devices with the spread of digitized electronic devices, such as liquid crystal televisions, PC displays, mobile phone terminals, portable game consoles, calculators, watches, It is used as a display unit for various devices. In particular, in recent years, there has been an LCD obtained by adhering a patterned retardation plate made of glass for the purpose of imparting a 3D function.
Here, the LCD to which the retardation plate is bonded may be collected after use, and only the LCD may be reused. For example, it is required to remove the retardation plate from the LCD and rework the LCD. At this time, in the conventional method, the entire LCD is cooled (in other words, the adhesive is cooled), and the retardation plate is peeled off from the LCD. However, this method requires equipment for cooling and cannot be said to have good workability. Furthermore, since both the retardation film and the LCD have rigidity, there is a problem that one of them is damaged when it is peeled off. In other words, it has been difficult for the conventional adhesive sheet to be easily peeled off after the LCD and the retardation plate are bonded, and to rework the LCD.
In order to solve such problems, an adhesive sheet that can be easily peeled even at room temperature and even if the adherend is as hard as glass has been studied. For example, Patent Document 1 proposes a transparent adhesive film containing an adhesive component and a gas generating agent that generates gas when irradiated with ultraviolet rays. Patent Document 2 proposes a thermal and actinic radiation curable (photocurable) adhesive composition.

特開２０１６−５６２４４号公報JP, 2006-56244, A 特表２０１１−５０８８１４号公報Special table 2011-508814 gazette

しかしながら、特許文献１に記載された透明接着フィルムは、リワーク時に露光する必要があり、また、特許文献２に記載された化学線硬化型（光硬化型）接着剤組成物は、リワーク時に加熱し、ワイヤーを用いて接着剤を切り進むことにより接着剤を除去している。すなわち、これまで、良好な接着性を確保しつつ、被着体から、常温で容易にＬＣＤを引き剥がすことが可能な接着シートが得られていないという現状がある。   However, the transparent adhesive film described in Patent Document 1 needs to be exposed during rework, and the actinic radiation curable (photo-curable) adhesive composition described in Patent Document 2 is heated during rework. The adhesive is removed by cutting the adhesive with a wire. That is, there has been a situation in which an adhesive sheet capable of easily peeling off the LCD at normal temperature from an adherend has not been obtained so far while ensuring good adhesiveness.

上記事情に鑑み、本発明は、常温でも被着体からＬＣＤを容易に引き剥がしてリワークすることができ、且つ、良好な接着性を付与することのできるＵＶ硬化型樹脂組成物、及びそれを含む接着シートを提供することを目的とする。   In view of the above circumstances, the present invention is a UV curable resin composition capable of easily peeling off an LCD from an adherend even at room temperature and reworking it, and imparting good adhesiveness, and It aims at providing the adhesive sheet containing.

本発明者らは、上記課題を解決するために鋭意検討した結果、（Ａ）ＵＶ硬化型プレポリマーと、（Ｂ）ＵＶ硬化型多官能モノマーと、（Ｃ）光重合開始剤と、（Ｄ）シランカップリング剤と、を含有し、前記（Ａ）成分はウレタン（メタ）アクリレートであり、前記（Ａ）成分１００質量部に対して、前記（Ｂ）成分の含有量が１５〜６０質量部、前記（Ｃ）成分の含有量が０．５質量部以上、前記（Ｄ）成分の含有量が０．１〜５質量部である、ＵＶ硬化型樹脂組成物が、上記課題を解決できることを見出し、本発明を完成させた。   As a result of intensive studies to solve the above problems, the present inventors have found that (A) a UV curable prepolymer, (B) a UV curable polyfunctional monomer, (C) a photopolymerization initiator, (D ) Silane coupling agent, the component (A) is urethane (meth) acrylate, and the content of the component (B) is 15 to 60 masses per 100 parts by mass of the component (A). UV curable resin composition in which the content of the component (C) is 0.5 parts by mass or more and the content of the component (D) is 0.1 to 5 parts by mass can solve the above problems. The present invention was completed.

即ち、本発明は以下のとおりである。
［１］
（Ａ）ＵＶ硬化型プレポリマーと、（Ｂ）ＵＶ硬化型多官能モノマーと、（Ｃ）光重合開始剤と、（Ｄ）シランカップリング剤と、を含有し、
前記（Ａ）成分はウレタン（メタ）アクリレートであり、
前記（Ａ）成分１００質量部に対して、前記（Ｂ）成分の含有量が１５〜６０質量部、前記（Ｃ）成分の含有量が０．５質量部以上、前記（Ｄ）成分の含有量が０．１〜５質量部である、ＵＶ硬化型樹脂組成物。
［２］
前記ウレタン（メタ）アクリレートは、ポリカーボネート骨格を有するウレタン（メタ）アクリレート、ポリエーテル骨格を有するウレタン（メタ）アクリレート、及びポリエステル骨格を有するウレタン（メタ）アクリレートからなる群から選択される１種以上である、上記［１］記載のＵＶ硬化型樹脂組成物。
［３］
前記ウレタン（メタ）アクリレートの重量平均分子量が１０，０００〜１００，０００であり、２重結合当量が１，０００〜５，０００ｇ／ｅｑである、上記［１］又は［２］記載のＵＶ硬化型樹脂組成物。
［４］
前記（Ｂ）ＵＶ硬化型多官能モノマーは、２個以上の官能基を有する（メタ）アクリルモノマーである、上記［１］〜［３］のいずれか記載のＵＶ硬化型樹脂組成物。
［５］
前記（Ｃ）光重合開始剤は、アシルフォスフィンオキサイド系光重合開始剤である、上記［１］〜［４］のいずれか記載のＵＶ硬化型樹脂組成物。
［６］
前記アシルフォスフィンオキサイド系光重合開始剤は、２，４，６−トリメチルベンゾイルジフェニルホスフィンオキサイドである、上記［５］記載のＵＶ硬化型樹脂組成物。
［７］
前記（Ｄ）シランカップリング剤は、（メタ）アクリル基を有するシランカップリング剤である、上記［１］〜［６］のいずれか記載のＵＶ硬化型樹脂組成物。
［８］
上記［１］〜［７］のいずれか記載のＵＶ硬化型樹脂組成物を含む接着シート。
［９］
乾燥後の膜厚が１０〜２５０μｍである、上記［８］記載の接着シート。
［１０］
ＬＣＤとパターニング位相差板とが積層された３Ｄ液晶パネルであって、
上記［８］または［９］記載の接着シートによって前記ＬＣＤと前記位相差板が接着された３Ｄ液晶パネル。
［１１］
前記パターニング位相差板は、パターンが形成されたガラス板である、上記［１０］記載の３Ｄ液晶パネル。 That is, the present invention is as follows.
[1]
(A) a UV curable prepolymer, (B) a UV curable polyfunctional monomer, (C) a photopolymerization initiator, and (D) a silane coupling agent,
The component (A) is urethane (meth) acrylate,
The content of the component (B) is 15 to 60 parts by mass with respect to 100 parts by mass of the component (A), the content of the component (C) is 0.5 parts by mass or more, and the content of the component (D) UV curable resin composition whose quantity is 0.1-5 mass parts.
[2]
The urethane (meth) acrylate is one or more selected from the group consisting of a urethane (meth) acrylate having a polycarbonate skeleton, a urethane (meth) acrylate having a polyether skeleton, and a urethane (meth) acrylate having a polyester skeleton. The UV curable resin composition according to the above [1].
[3]
The UV curing according to the above [1] or [2], wherein the urethane (meth) acrylate has a weight average molecular weight of 10,000 to 100,000 and a double bond equivalent of 1,000 to 5,000 g / eq. Mold resin composition.
[4]
The UV curable resin composition according to any one of [1] to [3], wherein the (B) UV curable polyfunctional monomer is a (meth) acrylic monomer having two or more functional groups.
[5]
The UV curable resin composition according to any one of [1] to [4], wherein the (C) photopolymerization initiator is an acylphosphine oxide photopolymerization initiator.
[6]
The UV curable resin composition according to the above [5], wherein the acylphosphine oxide photopolymerization initiator is 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
[7]
The UV curable resin composition according to any one of [1] to [6] above, wherein the (D) silane coupling agent is a silane coupling agent having a (meth) acryl group.
[8]
The adhesive sheet containing the UV curable resin composition in any one of said [1]-[7].
[9]
The adhesive sheet according to [8] above, wherein the film thickness after drying is 10 to 250 μm.
[10]
A 3D liquid crystal panel in which an LCD and a patterning retardation plate are laminated,
A 3D liquid crystal panel in which the LCD and the retardation plate are adhered by the adhesive sheet according to the above [8] or [9].
[11]
The 3D liquid crystal panel according to [10], wherein the patterning retardation plate is a glass plate on which a pattern is formed.

本発明のＵＶ硬化型樹脂組成物を含む接着シートは、常温でも被着体からＬＣＤを容易に引き剥がしてリワークすることができ、且つ、良好な接着性を付与することができる。   The adhesive sheet containing the UV curable resin composition of the present invention can be easily reworked by peeling off the LCD from the adherend even at room temperature, and can provide good adhesion.

以下、本発明を実施するための形態（以下、「本実施形態」という。）について詳細に記載する。なお、本発明は以下の実施の形態に限定されるものではなく、その要旨の範囲内で種々変形して実施することができる。   Hereinafter, modes for carrying out the present invention (hereinafter referred to as “the present embodiment”) will be described in detail. In addition, this invention is not limited to the following embodiment, It can implement by changing variously within the range of the summary.

本実施形態におけるＵＶ硬化型樹脂組成物は、
（Ａ）ＵＶ硬化型プレポリマーと、（Ｂ）ＵＶ硬化型多官能モノマーと、（Ｃ）光重合開始剤と、（Ｄ）シランカップリング剤と、を含有し、
前記（Ａ）成分はウレタン（メタ）アクリレートであり、
前記（Ａ）成分１００質量部に対して、前記（Ｂ）成分の含有量が１５〜６０質量部、前記（Ｃ）成分の含有量が０．５質量部以上、前記（Ｄ）成分の含有量が０．１〜５質量部である。 The UV curable resin composition in this embodiment is
(A) a UV curable prepolymer, (B) a UV curable polyfunctional monomer, (C) a photopolymerization initiator, and (D) a silane coupling agent,
The component (A) is urethane (meth) acrylate,
The content of the component (B) is 15 to 60 parts by mass with respect to 100 parts by mass of the component (A), the content of the component (C) is 0.5 parts by mass or more, and the content of the component (D) The amount is 0.1 to 5 parts by mass.

［（Ａ）ＵＶ硬化型プレポリマー］
本実施形態におけるＵＶ硬化型樹脂組成物は、（Ａ）ＵＶ硬化型プレポリマー（以下、「（Ａ）成分」ともいう。）を含む。ＵＶ硬化型プレポリマーは、ウレタン構造を主鎖に、（メタ）アクリル基を側鎖に含むウレタン（メタ）アクリレートであれば特に限定されない。ウレタン（メタ）アクリレートとしては、特に限定されず、例えば、ポリカーボネート骨格を有するウレタン（メタ）アクリレート、ポリエーテル骨格を有するウレタン（メタ）アクリレート、ポリエステル骨格を有するウレタン（メタ）アクリレート等が挙げられ、中でも、硬化接着シートの無黄変性の観点から、ポリカーボネート骨格を有するウレタン（メタ）アクリレートが好ましい。 [(A) UV curable prepolymer]
The UV curable resin composition in the present embodiment includes (A) a UV curable prepolymer (hereinafter also referred to as “component (A)”). The UV curable prepolymer is not particularly limited as long as it is a urethane (meth) acrylate having a urethane structure in the main chain and a (meth) acryl group in the side chain. The urethane (meth) acrylate is not particularly limited, and examples thereof include a urethane (meth) acrylate having a polycarbonate skeleton, a urethane (meth) acrylate having a polyether skeleton, a urethane (meth) acrylate having a polyester skeleton, and the like. Among these, urethane (meth) acrylate having a polycarbonate skeleton is preferable from the viewpoint of non-yellowing of the cured adhesive sheet.

ポリカーボネート骨格を有するウレタン（メタ）アクリレートとは、主鎖にポリカーボネート構造とウレタン構造を有し、側鎖に（メタ）アクリル基を有するプレポリマーのことをいう。ポリカーボネート骨格を有するウレタン（メタ）アクリレートは、例えば、ポリカーボネートジオールとジイソシアネートとカルボン酸ジオールとを反応させた後、グリシジル（メタ）アクリレートを反応させることにより得ることができる。   The urethane (meth) acrylate having a polycarbonate skeleton refers to a prepolymer having a polycarbonate structure and a urethane structure in the main chain and a (meth) acryl group in the side chain. A urethane (meth) acrylate having a polycarbonate skeleton can be obtained, for example, by reacting a polycarbonate diol, a diisocyanate, and a carboxylic acid diol and then reacting glycidyl (meth) acrylate.

ポリカーボネートジオールの重量平均分子量は、好ましくは１７０〜１，０００であり、より好ましくは３００〜７００であり、さらに好ましくは４００〜６００である。ポリカーボネートジオールの重量平均分子量が上記範囲であると、ウレタンプレポリマー主鎖に、リワークに必要な膜性が付与される傾向にある。   The weight average molecular weight of the polycarbonate diol is preferably 170 to 1,000, more preferably 300 to 700, and still more preferably 400 to 600. When the weight average molecular weight of the polycarbonate diol is in the above range, the urethane prepolymer main chain tends to have film properties necessary for rework.

ジイソシアネートとしては、特に限定されず、例えば、２，４―トリレンジイソシアネート（２，４−ＴＤＩ）、２，６−トリレンジイソシアネート（２，６−ＴＤＩ）、４，４’−ジフェニルメタンジイソシアネート（４，４’―ＭＤＩ）、２，４’―ジフェニルメタンジイソシアネート（２，４’−ＭＤＩ）、１，４−フェニレンジイソシアネート、キシリレンジイソシアネート（ＸＤＩ）、テトラメチルキシリレンジイソシアネート（ＴＭＸＤＩ）、トリジンジイソシアネート（ＴＯＤＩ）、１，５−ナフタレンジイソシアネート（ＮＤＩ）などの芳香族イソシアネート；ヘキサメチレンイソシアネート（ＨＤＩ）、トリメチルヘキサメチレンジイソシアネート（ＴＭＨＤＩ）、リジンジイソシアネート、ノルボルナンジイソシアナートメチル（ＮＢＤＩ）などの脂肪族ポリイソシアネート；トランスシクロヘキサン−１，４−ジイソシアネート、イソホロンジイソシアネート（ＩＰＤＩ）、Ｈ６ＸＤＩ（水添ＸＤＩ）などの脂環式ポリイソシアネート等が挙げられ、中でも、光学特性（黄変しにくさ）の観点から、ヘキサメチレンジイソシアネートが好ましい。   The diisocyanate is not particularly limited, and for example, 2,4-tolylene diisocyanate (2,4-TDI), 2,6-tolylene diisocyanate (2,6-TDI), 4,4′-diphenylmethane diisocyanate (4 , 4'-MDI), 2,4'-diphenylmethane diisocyanate (2,4'-MDI), 1,4-phenylene diisocyanate, xylylene diisocyanate (XDI), tetramethylxylylene diisocyanate (TMXDI), tolidine diisocyanate (TODI) ), Aromatic isocyanates such as 1,5-naphthalene diisocyanate (NDI); hexamethylene isocyanate (HDI), trimethylhexamethylene diisocyanate (TMHDI), lysine diisocyanate, norbornane diisocyanate Aliphatic polyisocyanates such as methyl (NBDI); alicyclic polyisocyanates such as transcyclohexane-1,4-diisocyanate, isophorone diisocyanate (IPDI), H6XDI (hydrogenated XDI), etc., among others, optical properties (yellow Hexamethylene diisocyanate is preferable from the viewpoint of difficulty in transformation.

カルボン酸ジオールとしては、特に限定されず、例えば、ジメチロールブタン酸、ジメチロールプロピオン酸等が挙げられる。   The carboxylic acid diol is not particularly limited, and examples thereof include dimethylolbutanoic acid and dimethylolpropionic acid.

ポリエーテル骨格を有するウレタン（メタ）アクリレートとは、主鎖にポリエーテル構造とウレタン構造を有し、側鎖に（メタ）アクリル基を有するプレポリマーのことをいい、ポリエステル骨格を有するウレタン（メタ）アクリレートは、主鎖にポリエステル構造とウレタン構造を有し、側鎖に（メタ）アクリル基を有するプレポリマーのことをいう。これらのプレポリマーは、ポリカーボネートジオールの代わりに、それぞれ、ポリエーテルジオール、ポリエステルジオールを用いること以外は上記ポリカーボネート骨格を有するウレタン（メタ）アクリレートと同様の方法により得ることができる。このとき、ポリエーテルジオール、ポリエステルジオールの好ましい重量平均分子量は、上述したポリカーボネートジオールの好ましい重量平均分子量と同じである。   The urethane (meth) acrylate having a polyether skeleton refers to a prepolymer having a polyether structure and a urethane structure in the main chain and having a (meth) acryl group in the side chain. ) Acrylate refers to a prepolymer having a polyester structure and a urethane structure in the main chain and a (meth) acryl group in the side chain. These prepolymers can be obtained by the same method as the urethane (meth) acrylate having the above polycarbonate skeleton, except that polyether diol and polyester diol are used instead of polycarbonate diol, respectively. At this time, the preferable weight average molecular weight of polyether diol and polyester diol is the same as the preferable weight average molecular weight of polycarbonate diol mentioned above.

（Ａ）成分の重量平均分子量は、好ましくは１０，０００〜１００，０００であり、より好ましくは３０，０００〜７０，０００であり、さらに好ましくは４０，０００〜６０，０００である。重量平均分子量が上記範囲であると、製膜性、硬化性が良好となり、長期信頼性が良好となる傾向にある。
ここで、重量平均分子量は、平均分子量が約５００〜約１００万の標準ポリスチレンを用いてゲルパーミエーションクロマトグラフィー（ＧＰＣ）により測定した値をいう。 (A) The weight average molecular weight of a component becomes like this. Preferably it is 10,000-100,000, More preferably, it is 30,000-70,000, More preferably, it is 40,000-60,000. When the weight average molecular weight is in the above range, the film-forming property and curability are good, and the long-term reliability tends to be good.
Here, the weight average molecular weight refers to a value measured by gel permeation chromatography (GPC) using standard polystyrene having an average molecular weight of about 500 to about 1,000,000.

（Ａ）成分の２重結合当量は、好ましくは１，０００〜５，０００ｇ／ｅｑであり、より好ましくは１，５００〜２，５００ｇ／ｅｑであり、さらに好ましくは１，８００〜２，２００ｇ／ｅｑである。２重結合当量が上記範囲であると、硬化収縮の影響が少なく、長期信頼性に優れ、また、硬化が容易となり、リワークも容易となる傾向にある。
ここで、２重結合当量は、カルボキシル基含有（メタ）アクリレートの固形分質量（ｇ）/オキシラン環とエチレン性不飽和結合を有する化合物のモル数（ｇ/ｍｏｌ）により算出した値をいう。 The double bond equivalent of the component (A) is preferably 1,000 to 5,000 g / eq, more preferably 1,500 to 2,500 g / eq, still more preferably 1,800 to 2,200 g. / Eq. When the double bond equivalent is in the above range, the effect of curing shrinkage is small, the long-term reliability is excellent, the curing is easy, and the rework tends to be easy.
Here, the double bond equivalent means a value calculated by the solid content mass (g) of the carboxyl group-containing (meth) acrylate / the number of moles of the compound having an oxirane ring and an ethylenically unsaturated bond (g / mol).

（Ａ）成分のガラス転移温度（Ｔｇ）は、好ましくは−１０〜２０℃、より好ましくは−５〜１５℃、さらに好ましくは０〜１０℃である。ガラス転移温度が上記範囲であると、長期信頼性とリワーク性とのバランスが良好となる傾向にある。
ここで、ガラス転移温度は、動的粘弾性測定（ＤＭＡ）により測定した値をいう。 (A) The glass transition temperature (Tg) of a component becomes like this. Preferably it is -10-20 degreeC, More preferably, it is -5-15 degreeC, More preferably, it is 0-10 degreeC. If the glass transition temperature is in the above range, the balance between long-term reliability and reworkability tends to be good.
Here, the glass transition temperature refers to a value measured by dynamic viscoelasticity measurement (DMA).

［（Ｂ）ＵＶ硬化型多官能モノマー］
本実施形態におけるＵＶ硬化型樹脂組成物は、（Ｂ）ＵＶ硬化型多官能モノマー（以下、「（Ｂ）成分」ともいう。）を含む。ＬＣＤのリワークを可能とするためには、常温での粘弾性を高める必要があるが、本実施形態においては、ＵＶ硬化型プレポリマーに対してＵＶ硬化型多官能モノマーを加えることで、硬化後の架橋密度を高め、常温での粘弾性を高めている。ここで、ＵＶ硬化型樹脂組成物の粘弾性は、動的粘弾性測定（ＤＭＡ）により測定することができ、好ましくは、硬化後常温（２５℃）での貯蔵弾性率が１．０×１０8〜１．０×１０10Ｐａであり、より好ましくは４．０×１０8〜５．０×１０9Ｐａであり、さらに好ましくは６．０×１０8〜３．０×１０9Ｐａである。 [(B) UV curable polyfunctional monomer]
The UV curable resin composition in the present embodiment contains (B) a UV curable polyfunctional monomer (hereinafter also referred to as “component (B)”). In order to enable LCD rework, it is necessary to increase the viscoelasticity at room temperature, but in this embodiment, by adding a UV curable polyfunctional monomer to the UV curable prepolymer, The crosslink density is increased to increase the viscoelasticity at room temperature. Here, the viscoelasticity of the UV curable resin composition can be measured by dynamic viscoelasticity measurement (DMA), and preferably the storage elastic modulus at room temperature (25 ° C.) after curing is 1.0 × 10. 8 to 1.0 × 10 10 Pa, more preferably 4.0 × 10 8 to 5.0 × 10 9 Pa, and still more preferably 6.0 × 10 8 to 3.0 × 10 9 Pa. is there.

（Ｂ）成分としては、特に限定されず、例えば、（メタ）アクリルモノマーが挙げられ、中でも、架橋密度を高め、リワーク性を向上させる観点から、２個以上の官能基を有する（メタ）アクリルモノマーが好ましい。   The component (B) is not particularly limited, and examples thereof include (meth) acrylic monomers. Among these, (meth) acrylic having two or more functional groups from the viewpoint of increasing the crosslinking density and improving the reworkability. Monomers are preferred.

（Ｂ）成分としては、具体的には、官能基が２個のものとしては、１、４−ブタンジオールジ（メタ）アクリレート、エチレングリコールジ（メタ）アクリレート、グリセリンジ（メタ）アクリレート、トリシクロデカンジメタノールジアクリレートが挙げられ、官能基が３個のものとしては、トリメチロールプロパントリアクリレート、トリメチロールメタントリ（メタ）アクリレート、トリメチロールプロパンプロピレンオキサイド変性トリ（メタ）アクリレートが挙げられ、官能基が４個以上のものとしては、ジペンタエリスリトールテトラ（メタ）アクリレート、ペンタエリスリトールエチレンオキサイド変性テトラ（メタ）アクリレート、ペンタエリスリトールテトラ（メタ）アクリレート、ペンタエリスリトールエチレンオキサイド変性テトラ（メタ）アクリレート、ジトリメチロールプロパンテトラ（メタ）アクリレート、ジペンタエリスリトールヘキサアクリレート等が挙げられ、中でも、リワーク性の観点から、４個以上の官能基を有する（メタ）アクリルモノマーが好ましく、６個の官能基を有するジペンタエリスリトールヘキサアクリレートがより好ましい。   Specifically, as the component (B), those having two functional groups include 1,4-butanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, glycerin di (meth) acrylate, tri Cyclodecane dimethanol diacrylate is exemplified, and those having three functional groups include trimethylolpropane triacrylate, trimethylolmethane tri (meth) acrylate, trimethylolpropane propylene oxide modified tri (meth) acrylate, Examples of those having four or more functional groups include dipentaerythritol tetra (meth) acrylate, pentaerythritol ethylene oxide modified tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, and pentaerythritol ethylene oxide. Modified tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol hexaacrylate and the like. Among them, (meth) acrylic monomers having four or more functional groups are preferable from the viewpoint of reworkability. Dipentaerythritol hexaacrylate having 6 functional groups is more preferable.

（Ａ）成分１００質量部に対する（Ｂ）成分の含有量は、１５〜６０質量部であり、好ましくは１８〜４０質量部であり、より好ましくは２０〜３０質量部である。（Ｂ）成分の含有量が１５質量部未満であると、硬化後の接着性が高く、常温でのリワーク性に劣り、６０質量部を超えると、接着性が充分でなく、長期信頼性に劣る。また、（Ａ）成分１００質量部に対する（Ｂ）成分の含有量が上記範囲に調整されている場合、樹脂組成物の溶融粘度が一定範囲に保たれるため、貼合ムラや映像の乱れが生じ難くなるという利点がある。   (A) Content of (B) component with respect to 100 mass parts of components is 15-60 mass parts, Preferably it is 18-40 mass parts, More preferably, it is 20-30 mass parts. When the content of the component (B) is less than 15 parts by mass, the adhesiveness after curing is high and the reworkability at room temperature is inferior, and when it exceeds 60 parts by mass, the adhesiveness is not sufficient and long-term reliability Inferior. In addition, when the content of the component (B) with respect to 100 parts by mass of the component (A) is adjusted to the above range, the melt viscosity of the resin composition is maintained in a certain range, so that bonding unevenness and image disturbance are caused. There is an advantage that it is difficult to occur.

［（Ｃ）光重合開始剤］
本実施形態におけるＵＶ硬化型樹脂組成物は、（Ｃ）光重合開始剤（以下、「（Ｃ）成分」ともいう。）を含む。光重合開始剤としては、特に限定されず、例えば、アシルフォスフィンオキサイド系光重合開始剤、アルキルフェノン系光重合開始剤、分子内水素引き抜き型光重合開始剤等のいずれの光重合開始剤も用いることができ、中でも、反応性、硬化の均一性の観点から、アシルフォスフィンオキサイド系光重合開始剤が好ましい。具体的には、２，４，６−トリメチルベンゾイルフェニルホスフィンオキサイド、２，２−ジメトキシ−１，２−ジフェニルエタン−１−オン、フェニルグリオキシリックアシッドメチルエステル等が挙げられ、中でも、ラジカル発生効率が高く、深部硬化性の観点から、２，４，６−トリメチルベンゾイルフェニルホスフィンオキサイドが好ましい。 [(C) Photopolymerization initiator]
The UV curable resin composition in the present embodiment contains (C) a photopolymerization initiator (hereinafter also referred to as “component (C)”). The photopolymerization initiator is not particularly limited. For example, any photopolymerization initiator such as an acylphosphine oxide photopolymerization initiator, an alkylphenone photopolymerization initiator, and an intramolecular hydrogen abstraction photopolymerization initiator can be used. Among them, acylphosphine oxide photopolymerization initiators are preferable from the viewpoints of reactivity and uniformity of curing. Specific examples include 2,4,6-trimethylbenzoylphenylphosphine oxide, 2,2-dimethoxy-1,2-diphenylethane-1-one, phenylglyoxylic acid methyl ester, etc. Among them, radical generation From the viewpoint of high efficiency and deep curability, 2,4,6-trimethylbenzoylphenylphosphine oxide is preferable.

（Ａ）成分１００質量部に対する（Ｃ）成分の含有量は、０．５質量部以上であり、好ましくは１．０質量部以上であり、より好ましくは１．５質量部以上である。（Ｃ）光重合開始剤の含有量が上記であると、硬化反応性が良好となり、リワーク性、長期信頼性が向上する傾向にある。（Ｃ）成分の含有量の上限としては特に限定されないが、多すぎると光学特性が低下する傾向にあるため、７．０質量部以下であることが好ましい。   (A) Content of (C) component with respect to 100 mass parts of component is 0.5 mass part or more, Preferably it is 1.0 mass part or more, More preferably, it is 1.5 mass part or more. (C) When content of a photoinitiator is above, hardening reactivity becomes favorable and it exists in the tendency for rework property and long-term reliability to improve. The upper limit of the content of the component (C) is not particularly limited, but if it is too large, the optical properties tend to deteriorate, and therefore it is preferably 7.0 parts by mass or less.

［（Ｄ）シランカップリング剤］
本実施形態におけるＵＶ硬化型樹脂組成物は、上記（Ａ）〜（Ｃ）成分に加えて、（Ｄ）シランカップリング剤（以下、「（Ｄ）成分」ともいう。）をさらに含む。上述したとおり、本実施形態のＵＶ硬化型樹脂組成物は、ＵＶ硬化型多官能モノマーを含むことにより、常温での粘弾性を高め、ＬＣＰのリワークを可能としている。一方で、粘弾性が高い場合、被着体との接着性が低下する傾向にある。本実施形態においては、ＵＶ硬化型樹脂組成物中にシランカップリング剤を含有させることで接着力を維持し、特に被着体がガラス板である場合の長期信頼性が向上する。 [(D) Silane coupling agent]
The UV curable resin composition in the present embodiment further includes (D) a silane coupling agent (hereinafter also referred to as “(D) component”) in addition to the components (A) to (C). As described above, the UV curable resin composition of the present embodiment includes a UV curable polyfunctional monomer, thereby increasing viscoelasticity at room temperature and enabling LCP rework. On the other hand, when the viscoelasticity is high, the adhesiveness with the adherend tends to decrease. In this embodiment, adhesive force is maintained by including a silane coupling agent in the UV curable resin composition, and long-term reliability is improved particularly when the adherend is a glass plate.

（Ｄ）成分としては、特に限定されず、例えば、モノマー型シランカップリング剤、アルコキシオリゴマー型シランカップリング剤、多官能型シランカップリング剤等のいずれのシランカップリング剤も用いることができる。中でも、被着体がガラスである場合の接着性の向上と、長期信頼性を保つという観点から、（メタ）アクリル基を有するシランカップリング剤が好ましく、３−アクリロキシプロピルトリメトキシシランがより好ましい。   (D) It does not specifically limit as a component, For example, any silane coupling agents, such as a monomer type silane coupling agent, an alkoxy oligomer type silane coupling agent, and a polyfunctional silane coupling agent, can be used. Among them, a silane coupling agent having a (meth) acryl group is preferable from the viewpoint of improving adhesion when the adherend is glass and maintaining long-term reliability, and 3-acryloxypropyltrimethoxysilane is more preferable. preferable.

（Ａ）成分１００質量部に対する（Ｄ）成分の含有量は、０．１〜５質量部であり、好ましくは０．５〜３．０質量部であり、より好ましくは０．５〜１．５質量部である。（Ｄ）成分の含有量が上記範囲であると、長期信頼性とリワーク性のバランスが良好となる傾向にある。   (A) Content of (D) component with respect to 100 mass parts of component is 0.1-5 mass parts, Preferably it is 0.5-3.0 mass parts, More preferably, 0.5-1. 5 parts by mass. When the content of component (D) is in the above range, the balance between long-term reliability and reworkability tends to be good.

［その他の成分］
本実施形態におけるＵＶ硬化型樹脂組成物には、上述した（Ａ）〜（Ｄ）成分以外にも、シリカ、アルミナ、水和アルミナ等の各種フィラー、酸化防止剤、紫外線吸収剤、光安定剤、帯電防止剤、レベリング剤、消泡剤、着色顔料、有機溶媒等の、通常接着剤に添加されることがある添加剤を含んでいてもよい。 [Other ingredients]
In addition to the components (A) to (D) described above, the UV curable resin composition in the present embodiment includes various fillers such as silica, alumina, hydrated alumina, antioxidants, ultraviolet absorbers, and light stabilizers. In addition, additives such as an antistatic agent, a leveling agent, an antifoaming agent, a color pigment, and an organic solvent, which are usually added to an adhesive, may be included.

［接着シート］
本実施形態における接着シートは、上述したＵＶ硬化型樹脂組成物を含む。具体的には、例えば、ＰＥＴ等の保護フィルム上に樹脂組成物を塗布して乾燥させた後、反対面にも保護フィルムを設けることにより、両面に保護フィルムが設けられた接着シートを得ることができる。特に、ＵＶ硬化型樹脂組成物を、有機溶媒を用いてワニスとした後、保護フィルム上に塗布し、乾燥することが好ましい。このとき用いられる有機溶媒としては、特に限定されないが、例えば、トルエン、メチルエチルケトン、シクロヘキサノン、プロピレングリコールモノメチルエーテル、ジメチルアセトアミド等が挙げられる。中でも、溶解性の観点から、メチルエチルケトンが好ましい。また、ワニス中の有機溶媒の含有量は、（Ａ）成分１００質量部に対して、好ましくは３０〜９０質量部であり、より好ましくは４０〜７０質量部である。 [Adhesive sheet]
The adhesive sheet in this embodiment contains the UV curable resin composition described above. Specifically, for example, after applying and drying a resin composition on a protective film such as PET, by providing a protective film on the opposite side, an adhesive sheet having protective films on both sides is obtained. Can do. In particular, the UV curable resin composition is preferably made into a varnish using an organic solvent, and then applied onto a protective film and dried. The organic solvent used at this time is not particularly limited, and examples thereof include toluene, methyl ethyl ketone, cyclohexanone, propylene glycol monomethyl ether, dimethylacetamide and the like. Of these, methyl ethyl ketone is preferable from the viewpoint of solubility. Moreover, the content of the organic solvent in the varnish is preferably 30 to 90 parts by mass, and more preferably 40 to 70 parts by mass with respect to 100 parts by mass of the component (A).

保護フィルムとしては、特に限定されず、例えば、ポリエチレンテレフタレート、ポリエチレンナフタレート、及びポリブチレンテレフタレートからなる群から選択される１種以上の樹脂からなるフィルムが挙げられ、中でも、製造コストを低減する観点から、ポリエチレンテレフタレート樹脂からなるフィルムが好ましい。   The protective film is not particularly limited, and includes, for example, a film made of one or more resins selected from the group consisting of polyethylene terephthalate, polyethylene naphthalate, and polybutylene terephthalate. Therefore, a film made of polyethylene terephthalate resin is preferable.

保護フィルムには、樹脂組成物が塗布される面に離型処理が施されていてもよい。保護フィルムに離型処理が施されていることにより、使用時に保護フィルムを容易に剥離することが可能になるため、取扱い性が向上する。離型処理としては、特に限定されず、例えば、シリコーン系離型剤、フッ素系離型剤、長鎖アルキルグラフトポリマー系離型剤等の離型剤や、プラズマ処理により表面処理する方法等を用いることができる。   The protective film may be subjected to a release treatment on the surface to which the resin composition is applied. Since the release treatment is performed on the protective film, the protective film can be easily peeled at the time of use, so that the handleability is improved. The release treatment is not particularly limited. For example, a release agent such as a silicone release agent, a fluorine release agent, a long-chain alkyl graft polymer release agent, a surface treatment method by plasma treatment, etc. Can be used.

保護フィルムにＵＶ硬化型樹脂組成物を塗布する方法としては、塗布厚さに応じて、コンマコーター、ダイコーター、グラビアコーターなどを適宜採用することができる。   As a method of applying the UV curable resin composition to the protective film, a comma coater, a die coater, a gravure coater, or the like can be appropriately employed depending on the coating thickness.

ＵＶ硬化型樹脂組成物の乾燥は、インラインドライヤー等により実施することができ、その際の乾燥条件は、各成分の種類及び量等により適宜調整することができる。乾燥後の接着シートの厚さは、好ましくは１０〜２５０μｍであり、より好ましくは２５〜１２５μｍ、さらに好ましくは３０〜７５μｍである。接着シートの厚さが上記範囲であると、接着性が良好となり長期信頼性が向上する。本実施形態において長期信頼性とは、具体的には、ＬＣＤとパターニング位相差板の接着性が良好となるため、ズレが生じ難くなり、結果観察者が良好な３Ｄ映像を観察することができるということを含む。さらに接着シートの厚さが上記範囲であると、ＬＣＤとパターニング位相差板との距離が適切となり、３Ｄ映像を見た際に、適度な視野角を確保することができる。   Drying of the UV curable resin composition can be carried out with an in-line dryer or the like, and the drying conditions at that time can be appropriately adjusted depending on the type and amount of each component. The thickness of the adhesive sheet after drying is preferably 10 to 250 μm, more preferably 25 to 125 μm, and still more preferably 30 to 75 μm. When the thickness of the adhesive sheet is within the above range, the adhesiveness is good and the long-term reliability is improved. In the present embodiment, the long-term reliability specifically means that the adhesion between the LCD and the patterning phase difference plate is good, so that it is difficult for the deviation to occur, and the result observer can observe a good 3D image. Including that. Furthermore, when the thickness of the adhesive sheet is within the above range, the distance between the LCD and the patterning phase difference plate is appropriate, and an appropriate viewing angle can be secured when a 3D image is viewed.

［３Ｄ液晶パネル］
本実施形態における３Ｄ液晶パネルは、ＬＣＤとパターニング位相差板とが積層されたものであって、前記ＬＣＤと前記位相差板が、本実施形態における接着シートによって接着されている。３Ｄ液晶パネルは、例えば、位相差板に接着シートを貼り合わせた後、その上からＬＣＤを貼り合わせ、さらに、ＵＶを照射することによって接着シートをＵＶ硬化させることにより得ることができる。 [3D LCD panel]
The 3D liquid crystal panel in the present embodiment is obtained by laminating an LCD and a patterning retardation plate, and the LCD and the retardation plate are bonded by the adhesive sheet in the present embodiment. The 3D liquid crystal panel can be obtained, for example, by pasting an adhesive sheet on a retardation plate, pasting an LCD on top of the adhesive sheet, and further curing the adhesive sheet by UV irradiation.

パターニング位相差板としては、パターンが形成されたガラス板を用いることができる。
なお、本実施形態におけるＵＶ硬化型樹脂組成物は、３Ｄ液晶パネルの用途のみだけでなく、ＬＣＤ、有機ＥＬなどの表示装置をリワークすることを想定した全ての用途において用いることができる。そのような用途としては、例えば、タッチセンサーパネル、デジタルサイネージ等が挙げられる。 As the patterning retardation plate, a glass plate on which a pattern is formed can be used.
In addition, the UV curable resin composition in the present embodiment can be used not only for the application of the 3D liquid crystal panel but also for all applications assuming reworking a display device such as an LCD or an organic EL. Examples of such applications include touch sensor panels and digital signage.

以下、本発明を実施例及び比較例によってさらに具体的に説明するが、本発明はこれらの実施例のみに限定されるものではない。   EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention further more concretely, this invention is not limited only to these Examples.

実施例及び比較例において用いた各成分・材料は以下のとおりである。
［（Ａ）成分：ＵＶ硬化型プレポリマー］
以下の合成例１〜３及び比較合成例１に従って、ＵＶ硬化型プレポリマー（ａ）〜（ｄ）を作製した。 The components and materials used in Examples and Comparative Examples are as follows.
[(A) component: UV curable prepolymer]
According to the following synthesis examples 1 to 3 and comparative synthesis example 1, UV curable prepolymers (a) to (d) were produced.

［（Ｂ）成分：ＵＶ硬化型多官能モノマー］
（１）ＵＶ硬化型多官能モノマー（ａ）
ジペンタエリスリトールヘキサアクリレート
ダイセルオルネクス社製、製品名「ＤＰＨＡ」
（２）ＵＶ硬化型多官能モノマー（ｂ）
トリシクロデカンジメタノールジアクリレート
ダイセルオルネクス社製、製品名「ＩＲＲ２１４−Ｋ」
（３）ＵＶ硬化型多官能モノマー（ｃ）
トリメチロールプロパントリアクリレート
ダイセルオルネクス社製、製品名「ＴＭＰＴＡ」
（４）ＵＶ硬化型多官能モノマー（ｄ）
エトキシ化フェニルアクリレート（一官能）
ダイセルオルネクス社製、製品名「ＥＢＥＣＲＹＬ１１０」 [(B) component: UV curable polyfunctional monomer]
(1) UV curable polyfunctional monomer (a)
Dipentaerythritol hexaacrylate, manufactured by Daicel Ornex, product name "DPHA"
(2) UV curable polyfunctional monomer (b)
Tricyclodecane dimethanol diacrylate, manufactured by Daicel Ornex Co., Ltd., product name “IRR214-K”
(3) UV curable polyfunctional monomer (c)
Trimethylolpropane triacrylate, product name “TMPTA” manufactured by Daicel Ornex Co., Ltd.
(4) UV curable polyfunctional monomer (d)
Ethoxylated phenyl acrylate (monofunctional)
Product name "EBECRYL110" manufactured by Daicel Ornex

［（Ｃ）成分：光重合開始剤］
（１）光重合開始剤（ａ）
２，４，６−トリメチルベンゾイルフェニルホスフィンオキサイド
ＢＡＳＦ社製、商品名「Ｉｒｇａｃｕｒｅ ＴＰＯ」、アシルフォスフィンオキサイド系光重合開始剤
（２）光重合開始剤（ｂ）
２，２−ジメトキシ−１，２−ジフェニルエタン−１−オン
ＢＡＳＦ社製、商品名「Ｉｒｇａｃｕｒｅ ６５１」、アルキルフェノン系光重合開始剤
（３）光重合開始剤（ｃ）
フェニルグリオキシリックアシッドメチルエステル
ＢＡＳＦ社製、商品名「Ｉｒｇａｃｕｒｅ ＭＢＦ」、分子内水素引き抜き型光重合開始剤 [(C) component: photopolymerization initiator]
(1) Photopolymerization initiator (a)
2,4,6-Trimethylbenzoylphenylphosphine oxide manufactured by BASF, trade name “Irgacure TPO”, acylphosphine oxide photopolymerization initiator (2) photopolymerization initiator (b)
2,2-dimethoxy-1,2-diphenylethane-1-one manufactured by BASF, trade name “Irgacure 651”, alkylphenone photopolymerization initiator (3) photopolymerization initiator (c)
Phenylglyoxylic acid methyl ester manufactured by BASF, trade name “Irgacure MBF”, intramolecular hydrogen abstraction type photopolymerization initiator

［（Ｄ）成分：シランカップリング剤］
（１）シランカップリング剤（ａ）
モノマー型シランカップリング剤
信越化学工業社製、商品名「ＫＢＭ−５１０３」、３−アクリロキシプロピルトリメトキシシラン
（２）シランカップリング剤（ｂ）
アルコキシオリゴマー型シランカップリング剤
信越化学工業社製、商品名「ＫＲ−５１３」
（３）シランカップリング剤（ｃ）
多官能型シランカップリング剤
信越化学工業社製、商品名「Ｘ−１２−１０５０」 [(D) component: silane coupling agent]
(1) Silane coupling agent (a)
Monomer type silane coupling agent, manufactured by Shin-Etsu Chemical Co., Ltd., trade name “KBM-5103”, 3-acryloxypropyltrimethoxysilane (2) silane coupling agent (b)
Alkoxy oligomer type silane coupling agent, trade name “KR-513” manufactured by Shin-Etsu Chemical Co., Ltd.
(3) Silane coupling agent (c)
Multifunctional silane coupling agent, trade name “X-12-1050” manufactured by Shin-Etsu Chemical Co., Ltd.

各評価方法及び測定方法は以下のとおりである。   Each evaluation method and measurement method are as follows.

［リワーク性］
（１）サンプル作製手順
接着シートの片側ＰＥＴフィルムを剥離し、ガラス（０．７ｔ、１９インチ）へラミネートにより貼り合わせ、オートクレーブ処理を行った。ラミネートはロールラミネートを用いて、ラミロール温度２５〜４０℃、ラミロール線圧１．０〜２．０ｋｇｆ／ｃｍ、ラミロール速度０．３〜２．０ｍ／ｍｉｎで実施し、オートクレーブは温度６０℃、圧力０．６ＭＰａ、時間１０ｍｉｎで実施した。もう片方のＰＥＴフィルムを剥離し、ＬＣＤと真空ラミネートにより貼合し、再度オートクレーブ処理を行った後、ＵＶ露光することにより試験サンプルを得た。真空ラミネートは、温度２５〜５０℃、圧力０．０１〜０．０５ＭＰａ、真空引き６０ｓ、加圧３０ｓで実施した。オートクレーブは、温度６０℃、圧力０．６ＭＰａ、時間１ｈｒで実施した。ＵＶ露光は超高圧水銀ランプ光源を用いて、積算光量が３０００ｍＪ／ｃｍ2となるように実施した。
（２）測定方法
試験サンプルを常温に２４ｈｒ以上放置後、ガラスを引き剥がした後の被着体（ガラス、ＬＣＤ）の破損を観察し、以下に従って評価した。
◎：被着体を破損せず、容易にリワークが可能であった
○：被着体を破損せずリワーク可能であった
×：リワーク困難であった [Reworkability]
(1) Sample preparation procedure The one-sided PET film of the adhesive sheet was peeled off and bonded to glass (0.7 t, 19 inches) by lamination, and autoclaved. Lamination is carried out using a roll laminate at a lami roll temperature of 25 to 40 ° C., a lami roll linear pressure of 1.0 to 2.0 kgf / cm, and a lami roll speed of 0.3 to 2.0 m / min. The autoclave is at a temperature of 60 ° C. and a pressure The test was carried out at 0.6 MPa for 10 minutes. The other PET film was peeled off, bonded by LCD and vacuum lamination, autoclaved again, and then UV-exposed to obtain a test sample. The vacuum lamination was performed at a temperature of 25 to 50 ° C., a pressure of 0.01 to 0.05 MPa, a vacuum drawing of 60 s, and a pressure of 30 s. The autoclave was carried out at a temperature of 60 ° C., a pressure of 0.6 MPa, and a time of 1 hr. The UV exposure was performed using an ultra-high pressure mercury lamp light source so that the integrated light amount was 3000 mJ / cm 2 .
(2) Measurement method After leaving the test sample at room temperature for 24 hours or more, the adherend (glass, LCD) after the glass was peeled off was observed and evaluated according to the following.
◎: The adherend was not damaged and could be easily reworked ○: The adherend was not damaged and rework was possible ×: Rework was difficult

［接着性］
（１）サンプル作製手順
リワーク性と同様の手順により試験サンプルを作製した。
（２）測定方法
試験サンプルを湿熱器に立てた状態で放置した。条件は、温度５０℃、湿度８０％、時間２４０ｈｒとした。その後、常温で２４ｈｒ放置した。湿熱器への放置開始時と比較した場合のガラス貼合位置のズレや、浮き、発泡の有無を観察し、以下に従って評価した。
○：ガラスの位置ズレ、浮き、発泡が発生しなかった
×：ガラスの位置ズレ、浮き、発泡が発生した [Adhesiveness]
(1) Sample preparation procedure A test sample was prepared by the same procedure as the reworkability.
(2) Measuring method The test sample was left standing in a humidifier. The conditions were a temperature of 50 ° C., a humidity of 80% and a time of 240 hours. Then, it was left at room temperature for 24 hours. The difference in the glass bonding position when compared with the start of standing in a humidifier, the presence or absence of floating and foaming were observed and evaluated according to the following.
○: Misalignment, float, and foaming of glass did not occur. ×: Misalignment, float, and foaming of glass occurred.

［貼合性］
（１）サンプル作製手順
リワーク性と同様の手順により試験サンプルを作製した。
（２）測定方法
試験サンプルのディスプレイを点灯させ、以下に従って評価した。
○：表示画像に貼合ムラ、３Ｄズレが発生しなかった（二重像の発生がなかった）
×：表示画像に貼合ムラ、３Ｄズレが発生した（二重像の発生があった） [Adhesiveness]
(1) Sample preparation procedure A test sample was prepared by the same procedure as the reworkability.
(2) Measuring method The display of the test sample was turned on and evaluated according to the following.
○: Bonding unevenness and 3D displacement did not occur in the display image (no double image was generated)
X: Bonding unevenness and 3D shift occurred in the display image (there was a double image)

［光学特性］
（１）サンプル作製手順
接着シートの片側ＰＥＴフィルムを剥離し、光学ガラス（４０ｍｍ角）へ真空ラミネートにより貼り合わせた。真空ラミネートは、温度２５〜５０℃、圧力０．０１〜０．０５ＭＰａ、真空引き１０ｓ、加圧１０ｓで実施した。もう片方のＰＥＴフィルムを剥離し光学ガラスに上記真空ラミネートの条件と同条件にて貼り合わせた後、オートクレーブ処理を行い、次いでＵＶ露光することにより試験サンプルを得た。オートクレーブは温度６０℃、圧力０．６ＭＰａ、時間１ｈｒにて実施した。ＵＶ露光は超高圧水銀ランプ光源を用いて、積算光量が３０００ｍＪ／ｃｍ2となるように実施した。
分光光度計（日立ハイテクノロジー製 Ｕ−４１００）を用いて試験サンプルのイエローインデックス（ＹＩ）を測定した。測定条件はＣ光源、透過、波長λ＝３８０〜７６０ｎｍとした。
◎：ＹＩ値１．５未満
○：ＹＩ値１．５値以上２未満
×：ＹＩ値２以上 [optical properties]
(1) Sample preparation procedure The one-sided PET film of the adhesive sheet was peeled off and bonded to optical glass (40 mm square) by vacuum lamination. The vacuum lamination was performed at a temperature of 25 to 50 ° C., a pressure of 0.01 to 0.05 MPa, a vacuuming of 10 s, and a pressure of 10 s. The other PET film was peeled off and bonded to an optical glass under the same conditions as the above vacuum lamination, then subjected to autoclave treatment, and then UV exposed to obtain a test sample. The autoclave was carried out at a temperature of 60 ° C., a pressure of 0.6 MPa, and a time of 1 hr. The UV exposure was performed using an ultra-high pressure mercury lamp light source so that the integrated light amount was 3000 mJ / cm 2 .
The yellow index (YI) of the test sample was measured using a spectrophotometer (U-4100 manufactured by Hitachi High Technology). The measurement conditions were C light source, transmission, wavelength λ = 380 to 760 nm.
◎: YI value less than 1.5 ○: YI value 1.5 value or more and less than 2 ×: YI value 2 or more

（合成例１）ＵＶ硬化型プレポリマー（ａ）
温度計、冷却管、攪拌装置を備えた４つ口フラスコに、ヘキサメチレンジイソシアネート（東ソー株式会社製、品名：ＨＤＩ、略名：ＨＤＩ）３３．３質量部と、重量平均分子量４００のポリカーボネートジオール５９．４質量部と、ジメチロールブタン酸７．３質量部と、触媒としてジブチル錫ラウレート等の有機錫化合物１質量部と、有機溶媒としてメチルエチルケトン１００質量部を反応容器に入れ、７０℃で２４時間反応させた。
得られた合成物の反応状況を確認するため、ＩＲ測定機器を用いて分析を行った。ＩＲチャートにおいて当該合成物のＮＣＯ特性吸収（２２７０ｃｍ-1）が消失していることを確認し、合成物がカルボキシル基を有するウレタンアクリレートであることを確認した。
次に得られたカルボキシル基を有するウレタンアクリレート１００質量部と、グリシジルメタクリレート７．１質量部と、触媒としてトリエチルアミン０．７質量部と、重合禁止剤としてハイドロキノン０．０５重合部とを反応容器に入れ、７５℃で１２時間反応を行い、付加反応させることによりＵＶ硬化型プレポリマー（ａ）を得た。
なお、付加反応は、以下の方法に従って測定した酸価が５ｍｇＫＯＨ／ｇ以下になった時点で終了させた。また、得られたＵＶ硬化型プレポリマー（ａ）は、重量平均分子量５０，０００、固形分濃度５０質量％、２重結合当量２，０００ｇ／ｅｑ、Ｔｇ５℃であった。 (Synthesis Example 1) UV curable prepolymer (a)
In a four-necked flask equipped with a thermometer, a condenser, and a stirrer, 33.3 parts by mass of hexamethylene diisocyanate (product name: HDI, abbreviated name: HDI, manufactured by Tosoh Corporation) and polycarbonate diol 59 having a weight average molecular weight of 400 .4 parts by mass, 7.3 parts by mass of dimethylolbutanoic acid, 1 part by mass of an organic tin compound such as dibutyltin laurate as a catalyst, and 100 parts by mass of methyl ethyl ketone as an organic solvent are put in a reaction vessel, and the mixture is kept at 70 ° C. for 24 hours. Reacted.
In order to confirm the reaction state of the obtained synthesized product, analysis was performed using an IR measuring instrument. In the IR chart, it was confirmed that the NCO characteristic absorption (2270 cm −1 ) of the composite had disappeared, and it was confirmed that the composite was a urethane acrylate having a carboxyl group.
Next, 100 parts by weight of the urethane acrylate having a carboxyl group, 7.1 parts by weight of glycidyl methacrylate, 0.7 parts by weight of triethylamine as a catalyst, and 0.05 parts by weight of hydroquinone as a polymerization inhibitor are used in a reaction vessel. The mixture was reacted at 75 ° C. for 12 hours and subjected to addition reaction to obtain a UV curable prepolymer (a).
The addition reaction was terminated when the acid value measured according to the following method became 5 mgKOH / g or less. The obtained UV curable prepolymer (a) had a weight average molecular weight of 50,000, a solid content concentration of 50% by mass, a double bond equivalent of 2,000 g / eq, and a Tg of 5 ° C.

（酸価測定方法）
樹脂の固形分１ｇを秤量し、混合溶剤（質量比：トルエン／メタノール＝５０／５０）を加えて溶解後指示薬としてフェノールフタレイン溶液を適量添加し、０．１Ｎの水酸化カリウム水溶液で滴定し、下記式（α）により酸価を測定した。
ｘ＝１０×Ｖｆ×５６．１／（Ｗｐ×Ｉ）・・・（α）
（式（α）中、ｘは酸価（ｍｇＫＯＨ／ｇ）を示し、Ｖｆは０．１ＮのＫＯＨ水溶液の滴定量（ｍＬ）を示し、Ｗｐは測定した樹脂溶液の質量（ｇ）を示し、Ｉは測定した樹脂溶液中の不揮発分の割合を（質量％）を示す。） (Acid value measuring method)
Weigh 1 g of resin solids, add mixed solvent (mass ratio: toluene / methanol = 50/50), add appropriate amount of phenolphthalein solution as indicator after dissolution, and titrate with 0.1N aqueous potassium hydroxide solution. The acid value was measured by the following formula (α).
x = 10 × Vf × 56.1 / (Wp × I) (α)
(In the formula (α), x represents an acid value (mgKOH / g), Vf represents a titration amount (mL) of a 0.1 N KOH aqueous solution, Wp represents the mass (g) of the measured resin solution, I represents the ratio of non-volatile content in the measured resin solution (mass%).)

（合成例２）ＵＶ硬化型プレポリマー（ｂ）
ポリカーボネートジオールに代えてポリエーテルジオールを用いたこと以外は合成例１と同様の方法により、ＵＶ硬化型プレポリマー（ｂ）を得た。 (Synthesis Example 2) UV curable prepolymer (b)
A UV curable prepolymer (b) was obtained in the same manner as in Synthesis Example 1 except that polyether diol was used instead of polycarbonate diol.

（合成例３）ＵＶ硬化型プレポリマー（ｃ）
ポリカーボネートジオールに代えてポリエステルジオールを用いたこと以外は合成例１と同様の方法により、ＵＶ硬化型プレポリマー（ｃ）を得た。 (Synthesis Example 3) UV curable prepolymer (c)
A UV curable prepolymer (c) was obtained in the same manner as in Synthesis Example 1 except that polyester diol was used instead of polycarbonate diol.

（比較合成例１）ＵＶ硬化型プレポリマー（ｄ）
攪拌機、温度計、滴下漏斗、および窒素導入管を備えた反応容器に、重合溶媒としてメトキシプロパノールプロピレングリコールモノメチルエーテル（ＰＧＭ）１００．０ｇを仕込み、窒素気流下で攪拌しながら８０度まで昇温した。これに室温で予め混合しておいたスチレン１３．５質量部、アクリル酸エチル６７質量部、アクリル酸１１．５質量部、ラジカル重合開始剤としてアゾビスイソブチロニトリル０．５ｇを８０℃に保温した状態で３時間かけて滴下漏斗から滴下した。滴下終了後、反応溶液を攪拌しながら９０℃まで昇温し、反応溶液の温度を９０度に保ちながら更に２時間攪拌し共重合物を得た。
次に得られた共重合物１００質量部と、グリシジルメタクリレート７．８質量部と、触媒としてトリエチルアミン０．８質量部と、重合禁止剤としてハイドロキノン０．０５重合部とを反応容器に入れ、１００℃で１２時間反応を行い、付加反応させることによりＵＶ硬化型プレポリマー（ｄ）を得た。
なお、付加反応は、酸価が５ｍｇＫＯＨ／ｇ以下になった時点で終了させた。また、得られたＵＶ硬化型プレポリマー（ｄ）は、重量平均分子量４５，０００、固形分濃度４７質量％、Ｔｇ３℃であった。 (Comparative Synthesis Example 1) UV curable prepolymer (d)
A reaction vessel equipped with a stirrer, a thermometer, a dropping funnel, and a nitrogen introduction tube was charged with 100.0 g of methoxypropanol propylene glycol monomethyl ether (PGM) as a polymerization solvent, and the temperature was raised to 80 degrees with stirring under a nitrogen stream. . 13.5 parts by weight of styrene, 67 parts by weight of ethyl acrylate, 11.5 parts by weight of acrylic acid, and 0.5 g of azobisisobutyronitrile as a radical polymerization initiator were mixed at 80 ° C. It was dripped from the dropping funnel over 3 hours while keeping the temperature. After completion of dropping, the reaction solution was heated to 90 ° C. while stirring, and further stirred for 2 hours while maintaining the temperature of the reaction solution at 90 ° C. to obtain a copolymer.
Next, 100 parts by mass of the copolymer obtained, 7.8 parts by mass of glycidyl methacrylate, 0.8 part by mass of triethylamine as a catalyst, and 0.05 part by polymerization of hydroquinone as a polymerization inhibitor were put in a reaction vessel, and 100 A UV curable prepolymer (d) was obtained by reacting at 12 ° C. for 12 hours and carrying out an addition reaction.
The addition reaction was terminated when the acid value became 5 mgKOH / g or less. Moreover, the obtained UV curable prepolymer (d) had a weight average molecular weight of 45,000, a solid content concentration of 47% by mass, and a Tg of 3 ° C.

（実施例１）
（１）ＵＶ硬化型樹脂組成物の調製
反応容器の中に、ＵＶ硬化型プレポリマー（ａ）１００質量部を加え、さらに、ＵＶ硬化型多官能モノマー（ａ）２５質量部、光重合開始剤（ａ）１．５質量部、シランカップリング剤（ａ）１質量部、及び溶剤としてメチルエチルケトン１４０質量部を加えて撹拌し、樹脂組成物を得た。
（２）接着シートの作製
上記（１）で得られた樹脂組成物を、乾燥後の厚さが３０μｍ以上となるように３８μｍのＰＥＴフィルム上に塗布し、１３０℃で５分間乾燥させた後、反対面にもＰＥＴフィルムを設置し、両面にＰＥＴフィルムを備えた接着シートを得た。
得られた接着シートを用いて、リワーク性、接着性、貼合性、光学特性の評価を行った。 Example 1
(1) Preparation of UV curable resin composition In a reaction vessel, 100 parts by mass of UV curable prepolymer (a) is added, and further 25 parts by mass of UV curable polyfunctional monomer (a), a photopolymerization initiator. (A) 1.5 parts by mass, 1 part by mass of a silane coupling agent (a), and 140 parts by mass of methyl ethyl ketone as a solvent were added and stirred to obtain a resin composition.
(2) Preparation of adhesive sheet After the resin composition obtained in (1) above was applied on a 38 μm PET film so that the thickness after drying was 30 μm or more, and dried at 130 ° C. for 5 minutes. A PET film was also installed on the opposite side, and an adhesive sheet provided with a PET film on both sides was obtained.
Using the obtained adhesive sheet, reworkability, adhesiveness, bonding property, and optical properties were evaluated.

（実施例２〜２０）、（比較例１〜７） (Examples 2 to 20), (Comparative Examples 1 to 7)

表１〜３に記載されたとおりに各成分の種類および含有量を変更した以外は実施例１と同様の方法により、ＵＶ硬化型樹脂組成物及び接着シートを得た。
得られた接着シートを用いて、リワーク性、接着性、貼合性、光学特性の評価を行った。 A UV curable resin composition and an adhesive sheet were obtained in the same manner as in Example 1 except that the type and content of each component were changed as described in Tables 1 to 3.
Using the obtained adhesive sheet, reworkability, adhesiveness, bonding property, and optical properties were evaluated.

本発明のＵＶ硬化型樹脂組成物を含む接着シートは、液晶表示ディスプレイ等の接着剤としての産業上利用可能性を有する。   The adhesive sheet containing the UV curable resin composition of the present invention has industrial applicability as an adhesive for a liquid crystal display or the like.

Claims (11)

（Ａ）ＵＶ硬化型プレポリマーと、（Ｂ）ＵＶ硬化型多官能モノマーと、（Ｃ）光重合開始剤と、（Ｄ）シランカップリング剤と、を含有し、
前記（Ａ）成分はウレタン（メタ）アクリレートであり、
前記（Ａ）成分１００質量部に対して、前記（Ｂ）成分の含有量が１５〜６０質量部、前記（Ｃ）成分の含有量が０．５質量部以上、前記（Ｄ）成分の含有量が０．１〜５質量部である、ＵＶ硬化型樹脂組成物。 (A) a UV curable prepolymer, (B) a UV curable polyfunctional monomer, (C) a photopolymerization initiator, and (D) a silane coupling agent,
The component (A) is urethane (meth) acrylate,
The content of the component (B) is 15 to 60 parts by mass with respect to 100 parts by mass of the component (A), the content of the component (C) is 0.5 parts by mass or more, and the content of the component (D) UV curable resin composition whose quantity is 0.1-5 mass parts. 前記ウレタン（メタ）アクリレートは、ポリカーボネート骨格を有するウレタン（メタ）アクリレート、ポリエーテル骨格を有するウレタン（メタ）アクリレート、及びポリエステル骨格を有するウレタン（メタ）アクリレートからなる群から選択される１種以上である、請求項１記載のＵＶ硬化型樹脂組成物。   The urethane (meth) acrylate is one or more selected from the group consisting of a urethane (meth) acrylate having a polycarbonate skeleton, a urethane (meth) acrylate having a polyether skeleton, and a urethane (meth) acrylate having a polyester skeleton. The UV curable resin composition according to claim 1. 前記ウレタン（メタ）アクリレートの重量平均分子量が１０，０００〜１００，０００であり、２重結合当量が１，０００〜５，０００ｇ／ｅｑである、請求項１又は２記載のＵＶ硬化型樹脂組成物。   The UV curable resin composition according to claim 1 or 2, wherein the urethane (meth) acrylate has a weight average molecular weight of 10,000 to 100,000 and a double bond equivalent of 1,000 to 5,000 g / eq. object. 前記（Ｂ）ＵＶ硬化型多官能モノマーは、２個以上の官能基を有する（メタ）アクリルモノマーである、請求項１〜３のいずれか１項記載のＵＶ硬化型樹脂組成物。   The UV curable resin composition according to any one of claims 1 to 3, wherein the (B) UV curable polyfunctional monomer is a (meth) acrylic monomer having two or more functional groups. 前記（Ｃ）光重合開始剤は、アシルフォスフィンオキサイド系光重合開始剤である、請求項１〜４のいずれか１項記載のＵＶ硬化型樹脂組成物。   The UV curable resin composition according to any one of claims 1 to 4, wherein the (C) photopolymerization initiator is an acylphosphine oxide photopolymerization initiator. 前記アシルフォスフィンオキサイド系光重合開始剤は、２，４，６−トリメチルベンゾイルジフェニルホスフィンオキサイドである、請求項５記載のＵＶ硬化型樹脂組成物。   The UV curable resin composition according to claim 5, wherein the acylphosphine oxide photopolymerization initiator is 2,4,6-trimethylbenzoyldiphenylphosphine oxide. 前記（Ｄ）シランカップリング剤は、（メタ）アクリル基を有するシランカップリング剤である、請求項１〜６のいずれか１項記載のＵＶ硬化型樹脂組成物。   The UV curable resin composition according to claim 1, wherein the (D) silane coupling agent is a silane coupling agent having a (meth) acryl group. 請求項１〜７のいずれか１項記載のＵＶ硬化型樹脂組成物を含む接着シート。   The adhesive sheet containing the UV curable resin composition of any one of Claims 1-7. 乾燥後の膜厚が１０〜２５０μｍである、請求項８記載の接着シート。   The adhesive sheet of Claim 8 whose film thickness after drying is 10-250 micrometers. ＬＣＤとパターニング位相差板とが積層された３Ｄ液晶パネルであって、
請求項８または９記載の接着シートによって前記ＬＣＤと前記位相差板が接着された３Ｄ液晶パネル。 A 3D liquid crystal panel in which an LCD and a patterning retardation plate are laminated,
A 3D liquid crystal panel in which the LCD and the retardation film are bonded by the adhesive sheet according to claim 8. 前記パターニング位相差板は、パターンが形成されたガラス板である、請求項１０記載の３Ｄ液晶パネル。   The 3D liquid crystal panel according to claim 10, wherein the patterning retardation plate is a glass plate on which a pattern is formed.
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020105437A (en) * 2018-12-28 2020-07-09 フジコピアン株式会社 Thin film support adhesive film
JP2020105438A (en) * 2018-12-28 2020-07-09 フジコピアン株式会社 Thin film support adhesive film
WO2021065923A1 (en) * 2019-10-01 2021-04-08 三菱ケミカル株式会社 Polarizing film with adhesive layer, adhesive sheet, multilayer member and image display device
CN113372824A (en) * 2021-06-24 2021-09-10 苏州赛伍应用技术股份有限公司 Water-impact-resistant high-viscosity UV (ultraviolet) viscosity-reducing adhesive and preparation method and application thereof
JP2022047865A (en) * 2020-09-14 2022-03-25 株式会社飯沼ゲージ製作所 Device and method for workpiece bonding
CN114391026A (en) * 2019-09-19 2022-04-22 汉高股份有限及两合公司 Photocurable (meth) acrylate composition
US11643480B2 (en) 2020-05-14 2023-05-09 Threebond Co., Ltd. Photocurable composition

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6704013B2 (en) * 2017-06-01 2020-06-03 株式会社有沢製作所 Double-sided adhesive sheet, 3D liquid crystal panel and manufacturing method thereof
JP2020019141A (en) * 2018-07-30 2020-02-06 凸版印刷株式会社 Barrier film, wavelength conversion sheet, and manufacturing method of wavelength conversion sheet

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000038547A (en) * 1998-07-24 2000-02-08 Mitsubishi Rayon Co Ltd Photocuring adhesive composition and optical member using same
JP2008248199A (en) * 2007-03-30 2008-10-16 Jsr Corp Impact-resistive adhesive layer, impact-resistive adhesive laminate, and display device
JP2011219686A (en) * 2010-04-14 2011-11-04 Denki Kagaku Kogyo Kk Adhesive composition, and temporary fixation method of member using the same
WO2013122144A1 (en) * 2012-02-17 2013-08-22 株式会社スリーボンド Photocurable sheet-type adhesive composition for optical use

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100112149A (en) 2007-12-28 2010-10-18 이 아이 듀폰 디 네모아 앤드 캄파니 Thermally and actinically curable adhesive composition
JP5834606B2 (en) * 2011-08-05 2015-12-24 Dic株式会社 UV-curable adhesive resin composition, adhesive and laminate
JP5641382B1 (en) * 2013-04-22 2014-12-17 Dic株式会社 UV curable adhesive composition and adhesive
JP6340765B2 (en) * 2013-08-21 2018-06-13 三菱ケミカル株式会社 Double-sided adhesive sheet and image display device
TWI638874B (en) * 2014-06-11 2018-10-21 日本化藥股份有限公司 Ultraviolet-curable resin composition for touch panel, bonding method and article using the same
JP2016056244A (en) 2014-09-05 2016-04-21 積水化学工業株式会社 Transparent adhesive film

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000038547A (en) * 1998-07-24 2000-02-08 Mitsubishi Rayon Co Ltd Photocuring adhesive composition and optical member using same
JP2008248199A (en) * 2007-03-30 2008-10-16 Jsr Corp Impact-resistive adhesive layer, impact-resistive adhesive laminate, and display device
JP2011219686A (en) * 2010-04-14 2011-11-04 Denki Kagaku Kogyo Kk Adhesive composition, and temporary fixation method of member using the same
WO2013122144A1 (en) * 2012-02-17 2013-08-22 株式会社スリーボンド Photocurable sheet-type adhesive composition for optical use

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020105437A (en) * 2018-12-28 2020-07-09 フジコピアン株式会社 Thin film support adhesive film
JP2020105438A (en) * 2018-12-28 2020-07-09 フジコピアン株式会社 Thin film support adhesive film
JP7214302B2 (en) 2018-12-28 2023-01-30 フジコピアン株式会社 thin support adhesive film
JP7214303B2 (en) 2018-12-28 2023-01-30 フジコピアン株式会社 thin support adhesive film
CN114391026A (en) * 2019-09-19 2022-04-22 汉高股份有限及两合公司 Photocurable (meth) acrylate composition
WO2021065923A1 (en) * 2019-10-01 2021-04-08 三菱ケミカル株式会社 Polarizing film with adhesive layer, adhesive sheet, multilayer member and image display device
US11643480B2 (en) 2020-05-14 2023-05-09 Threebond Co., Ltd. Photocurable composition
JP2022047865A (en) * 2020-09-14 2022-03-25 株式会社飯沼ゲージ製作所 Device and method for workpiece bonding
CN113372824A (en) * 2021-06-24 2021-09-10 苏州赛伍应用技术股份有限公司 Water-impact-resistant high-viscosity UV (ultraviolet) viscosity-reducing adhesive and preparation method and application thereof

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