JP2003336013A - Transparent pressure-sensitive adhesive, transparent pressure-sensitive adhesive sheet and laminate - Google Patents

Transparent pressure-sensitive adhesive, transparent pressure-sensitive adhesive sheet and laminate

Info

Publication number
JP2003336013A
JP2003336013A JP2002147589A JP2002147589A JP2003336013A JP 2003336013 A JP2003336013 A JP 2003336013A JP 2002147589 A JP2002147589 A JP 2002147589A JP 2002147589 A JP2002147589 A JP 2002147589A JP 2003336013 A JP2003336013 A JP 2003336013A
Authority
JP
Japan
Prior art keywords
transparent
sensitive adhesive
sheet
transparent pressure
adhesive sheet
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.)
Pending
Application number
JP2002147589A
Other languages
Japanese (ja)
Inventor
Makoto Inanaga
誠 稲永
Original Assignee
Mitsubishi Plastics Ind Ltd
三菱樹脂株式会社
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mitsubishi Plastics Ind Ltd, 三菱樹脂株式会社 filed Critical Mitsubishi Plastics Ind Ltd
Priority to JP2002147589A priority Critical patent/JP2003336013A/en
Publication of JP2003336013A publication Critical patent/JP2003336013A/en
Pending legal-status Critical Current

Links

Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10743Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing acrylate (co)polymers or salts thereof
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10697Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer being cross-linked
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10706Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer being photo-polymerized

Abstract

<P>PROBLEM TO BE SOLVED: To enable lamination of a synthetic resin sheet and a glass sheet at room temperature and, simultaneously, possession of external appearance of good quality without requiring a high-temperature/high-pressure treatment by an autoclave. <P>SOLUTION: A transparent pressure-sensitive adhesive sheet is obtained by molding a transparent pressure-sensitive adhesive comprising a (meth)acrylate copolymer containing an &alpha;,&beta;-unsaturated carboxylic acid, a (meth)acrylate monomer having an organic functional group which reacts with the above unsaturated carboxylic acid, and a photoinitiator into a sheet having a thickness of 0.05-2 mm, and irradiating the sheet with ultraviolet rays to effect crosslinking. The sheet is made to have (a) a storage modulus G' (1 Hz) at a measuring temperature of 20&deg;C at a frequency of 1 Hz of 2&times;10<SP>3</SP>to 4&times;10<SP>4</SP>Pa and (b) a storage modulus G' (10<SP>-7</SP>Hz) at a standard temperature of 20&deg;C at a frequency of 10<SP>-7</SP>Hz of 5&times;10<SP>1</SP>to 2&times;10<SP>3</SP>Pa as the modulus. <P>COPYRIGHT: (C)2004,JPO

Description

【発明の詳細な説明】Detailed Description of the Invention
【0001】[0001]
【発明の属する技術分野】本発明は、透明粘着剤、透明
粘着シート及び積層体、詳しくは、自動車等の車両、船
舶、航空機、建築物、各種機械装置類等の窓材の合わせ
ガラスやプラズマ発光表示装置(PDP)、液晶表示装
置(LCD)、有機エレクトロルミネッセンス(EL)
等の平面型画像表示装置のパネルである透明積層体に好
適に使用される透明粘着剤、透明粘着シート及び積層体
に関する。
TECHNICAL FIELD The present invention relates to a transparent pressure-sensitive adhesive, a transparent pressure-sensitive adhesive sheet and a laminate, and more specifically, laminated glass and plasma for window materials for vehicles such as automobiles, ships, aircraft, buildings, and various mechanical devices. Light emitting display (PDP), liquid crystal display (LCD), organic electroluminescence (EL)
The present invention relates to a transparent pressure-sensitive adhesive, a transparent pressure-sensitive adhesive sheet, and a layered body which are preferably used for a transparent layered body which is a panel of a flat image display device such as.
【0002】[0002]
【従来の技術】ガラス板は、車両や船舶、さらには建築
用等の窓材として広く用いられている。これらの窓材の
耐衝撃性の向上、衝突物の貫通防止を図るため、2枚の
ガラス板間にポリビニルブチラール(PVB)からなる
膜を挟んだ安全合わせガラスが一般的に用いられてい
る。このような合わせガラスは、重量が大きく、衝撃の
際には貫通しにくいが、ガラス板にひび割れ等が発生す
ることがある。近年では、平面型画像表示装置におい
て、軽量化、耐衝撃性の向上を図るとともに、ガラス板
の表示パネルの割れを防止するため、保護パネルとして
合成樹脂板を使用することが提案されている。例えば、
ポリカーボネート(PC)板に代表される割れにくい合
成樹脂板を保護パネルとして用い、これをガラス板に貼
り合せた、合成樹脂板/ガラス板の積層体が提案されて
いる。合成樹脂板/ガラス板の積層体を得る方法として
は、合成樹脂板とガラス板の間にPVB膜、エチレン−
酢酸ビニル共重合体(EVA)膜、ウレタン系フィルム
等の熱可塑性樹脂を挟み、オートクレーブを用いて高温
・高圧条件で貼り合わせるのが一般的である。しかし、
上記のような熱可塑性樹脂を用いる方法では、通常80
℃以上の加熱が必要であるため、合成樹脂板とガラス板
の線膨張係数の相違により、加熱圧着後の積層体が室温
に戻った際に反りや割れを生じるという問題があった。
また、紫外線硬化型液状樹脂を透明な板の間に注入した
後、紫外線を照射して硬化させる方法が提案されている
が、この方法は、液状樹脂の注入方法や膜厚制御が容易
でないという問題がある。
2. Description of the Related Art Glass sheets are widely used as window materials for vehicles, ships, and construction. In order to improve the impact resistance of these window materials and prevent penetration of collision objects, safety laminated glass having a film made of polyvinyl butyral (PVB) sandwiched between two glass plates is generally used. Such a laminated glass has a large weight and is hard to penetrate through it when it is impacted, but cracks or the like may occur on the glass plate. In recent years, it has been proposed to use a synthetic resin plate as a protective panel in a flat panel image display device in order to reduce the weight and improve the impact resistance and prevent the display panel of the glass plate from cracking. For example,
A synthetic resin plate / glass plate laminate has been proposed in which a synthetic resin plate that is not easily broken, such as a polycarbonate (PC) plate, is used as a protective panel and is bonded to a glass plate. As a method for obtaining a laminated body of a synthetic resin plate / glass plate, a PVB film, ethylene-
Generally, a thermoplastic resin such as a vinyl acetate copolymer (EVA) film or a urethane film is sandwiched and then bonded together under high temperature and high pressure conditions using an autoclave. But,
In the method using the thermoplastic resin as described above, it is usually 80
Since heating at a temperature of ℃ or more is required, there is a problem that the laminated body after thermocompression bonding may warp or crack due to the difference in linear expansion coefficient between the synthetic resin plate and the glass plate.
Further, a method of injecting an ultraviolet curable liquid resin between transparent plates and then irradiating it with ultraviolet rays to cure it has been proposed, but this method has a problem that it is not easy to inject the liquid resin and control the film thickness. is there.
【0003】[0003]
【発明が解決しようとする課題】本発明は、上記従来技
術の問題点を考慮してなされたものであって、オートク
レーブによる高温・高圧処理を必要とすることなく、合
成樹脂板やガラス板の貼り合わせを室温でかつ良好な外
観品質を有するように行なうことが可能な、透明粘着
剤、透明粘着シート、さらには該透明粘着シートを適用
して得られる積層体を提供することを目的とする。
SUMMARY OF THE INVENTION The present invention has been made in consideration of the above-mentioned problems of the prior art, and it is possible to obtain a synthetic resin plate or a glass plate without the need for high temperature / high pressure treatment by an autoclave. An object of the present invention is to provide a transparent pressure-sensitive adhesive, a transparent pressure-sensitive adhesive sheet, and a laminate obtained by applying the transparent pressure-sensitive adhesive sheet, which can be laminated at room temperature so as to have good appearance quality. .
【0004】[0004]
【課題を解決するための手段】(1) 本発明は、α,β不
飽和カルボン酸を含有した(メタ)アクリル酸エステル
系共重合体に前記不飽和カルボン酸と反応する有機官能
基含有(メタ)アクリレートモノマー、光開始剤を含有
したことを特徴とする透明粘着剤である。
Means for Solving the Problems (1) The present invention provides a (meth) acrylic acid ester-based copolymer containing an α, β unsaturated carboxylic acid containing an organic functional group that reacts with the unsaturated carboxylic acid ( A transparent pressure-sensitive adhesive containing a (meth) acrylate monomer and a photoinitiator.
【0005】(2) 上記の粘着剤を厚さ0.05〜2mm
のシート状に成形し、紫外線を照射して架橋させたこと
を特徴とする透明粘着シートである。 (3) 前記紫外線を照射して架橋させたシートが下記
(a)及び(b)の弾性率の範囲にあることを特徴とす
る透明粘着シートである。 (a)測定温度20℃、周波数1Hzでの貯蔵弾性率
G’(1Hz)が2×103 〜4×104 Pa。 (b)基準温度20℃、周波数10-7Hzでの貯蔵弾性
率G’(10-7Hz)が5×101 〜2×103 Pa。 (4) 上記(2) 又は(3) に記載の透明粘着シートを中間層
として、少なくともその片面に透明なガラス板又は合成
樹脂板を積層してなる積層体である。
(2) The thickness of the above adhesive is 0.05-2 mm
The transparent pressure-sensitive adhesive sheet is characterized in that it is formed into a sheet shape and is cross-linked by irradiating ultraviolet rays. (3) A transparent pressure-sensitive adhesive sheet, characterized in that the sheet cross-linked by irradiating with the ultraviolet rays has an elastic modulus in the following ranges (a) and (b). (A) Storage elastic modulus G ′ (1 Hz) at a measurement temperature of 20 ° C. and a frequency of 1 Hz is 2 × 10 3 to 4 × 10 4 Pa. (B) The storage elastic modulus G ′ (10 −7 Hz) at a reference temperature of 20 ° C. and a frequency of 10 −7 Hz is 5 × 10 1 to 2 × 10 3 Pa. (4) A laminate in which the transparent pressure-sensitive adhesive sheet according to (2) or (3) above is used as an intermediate layer, and a transparent glass plate or a synthetic resin plate is laminated on at least one surface thereof.
【0006】[0006]
【発明の実施の形態】本発明に係る透明粘着剤は、合成
樹脂板/ガラス板、合成樹脂板/合成樹脂板、ガラス板
/ガラス板等の積層体の板間の中間層(中間膜)として
使用するのに適している。従来の合わせガラスのような
透明積層体では、中間層を加熱溶融させ、2枚のガラス
板間の凹凸を埋めるようないわゆるホットメルトタイプ
の接着剤を用いるものであるのに対し、本発明に係る透
明粘着剤は、室温で貼り合わせが可能な粘弾性挙動を有
するため、このような積層体を得る際、従来のような加
熱が不要である。
BEST MODE FOR CARRYING OUT THE INVENTION The transparent adhesive according to the present invention is an intermediate layer (intermediate film) between plates of a laminated body such as synthetic resin plate / glass plate, synthetic resin plate / synthetic resin plate, glass plate / glass plate and the like. Suitable for use as. In a conventional transparent laminated body such as a laminated glass, a so-called hot-melt type adhesive that heats and melts an intermediate layer and fills the unevenness between two glass plates is used. Since such a transparent pressure-sensitive adhesive has a viscoelastic behavior capable of being stuck at room temperature, it is not necessary to heat the laminate as in the conventional case.
【0007】本発明に係る透明粘着シートは、上記の粘
着剤を厚さ0.05〜2mmのシート状に成形した後に
紫外線を照射して架橋させることにより得られる。厚さ
0.05〜2mmのシート状への成形は、通常、離型フ
ィルム上に積層する形で形成され、実施例に例示するよ
うに、溶融状態の透明粘着剤を2枚の離型フィルム(少
なくとも一方は透明性の離型フィルム)間に挟まれるよ
う形成するのが好ましい態様である。透明なフィルムを
通して紫外線を照射することにより、所定の粘弾性を付
与することができる。
The transparent pressure-sensitive adhesive sheet according to the present invention is obtained by molding the above-mentioned pressure-sensitive adhesive into a sheet having a thickness of 0.05 to 2 mm and then irradiating it with ultraviolet rays to crosslink it. Molding into a sheet having a thickness of 0.05 to 2 mm is usually formed by laminating on a release film, and as illustrated in the examples, two transparent release films each containing a transparent adhesive in a molten state are used. It is a preferred embodiment that it is formed so as to be sandwiched between (at least one of them is a transparent release film). A predetermined viscoelasticity can be imparted by irradiating ultraviolet rays through a transparent film.
【0008】紫外線を照射して架橋させた後の透明粘着
シートは、積層体の板間の中間層(中間膜)として使用
される際、その板間の凹凸を埋めるような柔らかさを有
しており、好ましくは下記(a)及び(b)の弾性率の
範囲にある。このような特定の範囲の弾性率を有するも
のとすることにより、板の積層加工時に板間の厚みの凹
凸に馴染んで緩和し、気泡のない積層外観を得ることが
でき、積層後には実用上の耐久性を確保することができ
る。
The transparent pressure-sensitive adhesive sheet after being irradiated with ultraviolet rays and cross-linked has a softness such that it fills irregularities between the plates when used as an intermediate layer (intermediate film) between the plates of the laminate. And preferably in the range of the elastic moduli shown in (a) and (b) below. By having an elastic modulus in such a specific range, it is possible to adjust to the unevenness of the thickness between the plates during the laminating process of the plates and to alleviate them, and to obtain a laminated appearance without bubbles, and practically after the lamination. The durability of can be secured.
【0009】(a)測定温度20℃、周波数1Hzでの
貯蔵弾性率G’(1Hz)が2×103 〜4×104
a。 (b)基準温度20℃、周波数10-7Hzでの貯蔵弾性
率G’(10-7Hz)が5×101 〜2×103 Pa。
(A) The storage elastic modulus G '(1 Hz) at a measurement temperature of 20 ° C. and a frequency of 1 Hz is 2 × 10 3 to 4 × 10 4 P.
a. (B) The storage elastic modulus G ′ (10 −7 Hz) at a reference temperature of 20 ° C. and a frequency of 10 −7 Hz is 5 × 10 1 to 2 × 10 3 Pa.
【0010】上記の弾性率は、レオメトリックス社製の
粘弾性測定装置ダイナミックアナライザーRDAIIを用
いて以下の条件で測定する。 ・温度:20〜150℃ ・角振動数:ω=0.005〜500rad/sec ・パラレルプレート:25mmφ ・歪み量:3%
The above-mentioned elastic modulus is measured under the following conditions using a dynamic analyzer RDAII, which is a viscoelasticity measuring device manufactured by Rheometrics.・ Temperature: 20 to 150 ° C. ・ Angular frequency: ω = 0.005 to 500 rad / sec ・ Parallel plate: 25 mmφ ・ Strain amount: 3%
【0011】上記のRDAIIで20℃を基準温度とし
て温度−時間換算のマスターカーブを作成し、周波数f
値はf(Hz)=ω/2πにより算出し、それぞれ貯蔵
弾性率G’、損失弾性率G”及びG”/G’=tanδ
を読みとる。
With the above RDAII, a temperature-time converted master curve was prepared with 20 ° C. as a reference temperature, and the frequency f
The values are calculated by f (Hz) = ω / 2π, and storage elastic modulus G ′, loss elastic modulus G ″ and G ″ / G ′ = tan δ, respectively.
Read.
【0012】上記(a)について、周波数1Hzでの貯
蔵弾性率G’(1Hz)が2×10 3 未満であると、非
常にやわらかいため、シート自身や積層加工時のハンド
リングが容易でない。4×104 Paを超えると、逆に
硬くなりすぎて板材になじみにくくなる。
Regarding (a) above, storage at a frequency of 1 Hz
Storage elastic modulus G '(1Hz) is 2 x 10 3 Less than, non
Since it is always soft, the sheet itself and the hand during lamination processing
Ring is not easy. 4 x 10Four If it exceeds Pa, on the contrary,
It becomes too hard to fit in the plate material.
【0013】また、上記(b)について、周波数10-7
Hzでの貯蔵弾性率G’(10-7Hz)が5×101
a未満であると、クリープ性に劣り、シート形状の長期
間の寸法安定性に乏しく、板ズレや発泡を生じやすいと
いった問題がある。2×10 3 を超えると、使用時、硬
すぎて緩和できずに板間の僅かな厚みの凹凸により、凹
部に気泡や剥離が発生するという問題を生じる場合があ
る。上記のような理由から(a)(b)の範囲とするこ
とが好ましい。
Regarding (b) above, a frequency of 10-7
Storage modulus G '(10-7Hz) is 5 × 101 P
If it is less than a, the creep property is poor and the sheet shape is long-term.
The dimensional stability between the two is poor, and it is easy for plate misalignment and foaming to occur.
There is such a problem. 2 x 10 3 If it exceeds the
It can not be relaxed because it is too much, and it is concave due to the slight unevenness between the plates
There may be a problem that bubbles or peeling may occur in the part.
It For the above reasons, the range of (a) and (b) should be selected.
And are preferred.
【0014】本発明の透明粘着剤及び透明粘着シート
は、α,β不飽和カルボン酸を含有した(メタ)アクリ
ル酸エステル系共重合体を主成分とする。このような
(メタ)アクリル酸エステル系共重合体としては、例え
ば、イソ−オクチルアクリレート、n−オクチルアクリ
レート、n−ブチルアクリレート、2−エチルヘキシル
アクリレート等から少なくとも1種類以上とアクリル酸
を共重合させたもので、共重合体の溶融粘度のB型粘度
計で測定した値が130℃で10万〜50万mPa・s
のものが好ましく用いられる。Tgが−60〜−20℃
でアクリル酸を0.5〜5%含有したものが好ましい。
The transparent pressure-sensitive adhesive and the transparent pressure-sensitive adhesive sheet of the present invention are mainly composed of a (meth) acrylic acid ester type copolymer containing an α, β unsaturated carboxylic acid. As such a (meth) acrylic acid ester-based copolymer, for example, at least one kind of iso-octyl acrylate, n-octyl acrylate, n-butyl acrylate, 2-ethylhexyl acrylate and the like are copolymerized with acrylic acid. The value of the melt viscosity of the copolymer measured by a B-type viscometer is 100,000 to 500,000 mPa · s at 130 ° C.
Those of are preferably used. Tg is -60 to -20 ° C
It is preferable to contain 0.5 to 5% of acrylic acid.
【0015】そして、不飽和カルボン酸と反応する有機
官能基含有(メタ)アクリレートモノマー、光開始剤を
含有する。
Then, it contains an organic functional group-containing (meth) acrylate monomer which reacts with an unsaturated carboxylic acid, and a photoinitiator.
【0016】有機官能基含有(メタ)アクリレートモノ
マーとしては、グリシジル基含有(メタ)アクリレート
モノマー、ヒドロキシ基含有(メタ)アクリレートモノ
マー、イソシアネート基含有(メタ)アクリレートモノ
マー等の前記不飽和カルボン酸と反応する官能基を有す
るものを用いることができる。その含有量は、(メタ)
アクリル酸エステル系共重合体100重量部に対し、
0.01〜1.0重量部、好ましくは0.02〜0.1
重量部である。その含有量が0.01重量部未満である
と、上記(b)要件の周波数10-7Hzでの貯蔵弾性率
G’(10-7Hz)が5×101 Pa未満となりやす
く、凝集が得られない。逆に含有量が1.0重量部を超
えると、貯蔵弾性率G’(10-7Hz)が2×103
aを超え、柔軟性が低下する。
As the organic functional group-containing (meth) acrylate monomer, a glycidyl group-containing (meth) acrylate monomer, a hydroxy group-containing (meth) acrylate monomer, an isocyanate group-containing (meth) acrylate monomer or the like is reacted with the unsaturated carboxylic acid. Those having a functional group that can be used. Its content is (meta)
With respect to 100 parts by weight of the acrylate copolymer,
0.01-1.0 parts by weight, preferably 0.02-0.1
Parts by weight. If the content is less than 0.01 part by weight, the storage elastic modulus G ′ (10 −7 Hz) at the frequency of 10 −7 Hz of the above requirement (b) tends to be less than 5 × 10 1 Pa, resulting in aggregation. I can't get it. On the contrary, when the content exceeds 1.0 part by weight, the storage elastic modulus G '(10 -7 Hz) is 2 × 10 3 P.
If it exceeds a, the flexibility is lowered.
【0017】光開始剤としては、着色性及び臭気性の少
ないものが好ましく、その添加量は、(メタ)アクリル
酸エステル系共重合体100重量部に対し、0.05〜
2.0重量部、好ましくは0.1〜1.0重量部であ
る。添加量が0.05重量部未満であると前記アクリレ
ートモノマーを充分に反応させるために紫外線光量が多
く必要である。逆に2.0重量部を超えるとシートの厚
み方向に紫外線が透過しにくくなり、均一に反応しにく
い。光開始剤としては、ベンゾフェノン、ヒドロキシ−
シクロヘキシル−フェニルケトン等を用いることがで
き、これらを2種以上組み合せてもよい。
As the photoinitiator, those having little coloring and odor are preferable, and the addition amount thereof is 0.05 to 100 parts by weight of the (meth) acrylic acid ester copolymer.
The amount is 2.0 parts by weight, preferably 0.1 to 1.0 part by weight. If the amount added is less than 0.05 parts by weight, a large amount of ultraviolet light is necessary to sufficiently react the acrylate monomer. On the other hand, when it exceeds 2.0 parts by weight, it becomes difficult for ultraviolet rays to pass through in the thickness direction of the sheet, and it is difficult to react uniformly. As the photoinitiator, benzophenone, hydroxy-
Cyclohexyl-phenyl ketone and the like can be used, and two or more kinds thereof may be combined.
【0018】前記不飽和カルボン酸と(メタ)アクリレ
ートモノマーの有機官能基とを反応させて(メタ)アク
リロイル基をグラフトさせて、シート状に成形する。こ
のシート状体は、厚さ0.05〜2mmの範囲とする。
厚さが0.05mm未満であると板材板材を合わせにく
くなり、2mmを超えると紫外線架橋が困難となる。そ
して、シート状に成形した後に、直接あるいは透明な離
型フィルムを介して高圧水銀ランプ等を用いて紫外線を
照射して架橋させることにより、積層体の中間層として
好適な透明粘着シートを得ることができる。高圧水銀ラ
ンプ等による紫外線の照射に際し、前記モノマー及び光
開始剤の量に応じて照射量を調節することにより、前記
した特定の範囲の弾性率を有する透明粘着シートを得る
ことができる。紫外線照射装置の種類は特に限定されな
い。高圧水銀ランプやメタルハライドランプ等を用いる
ことができる。
The unsaturated carboxylic acid and the organic functional group of the (meth) acrylate monomer are reacted to graft a (meth) acryloyl group, and a sheet is formed. This sheet-shaped body has a thickness of 0.05 to 2 mm.
If the thickness is less than 0.05 mm, it will be difficult to match the plate materials, and if it exceeds 2 mm, ultraviolet crosslinking will be difficult. Then, after being formed into a sheet, by directly or through a transparent release film, a high-pressure mercury lamp or the like is used to irradiate with ultraviolet rays to crosslink, thereby obtaining a transparent adhesive sheet suitable as an intermediate layer of a laminate. You can Upon irradiation of ultraviolet rays from a high-pressure mercury lamp or the like, by adjusting the irradiation amount according to the amounts of the monomer and photoinitiator, it is possible to obtain a transparent pressure-sensitive adhesive sheet having an elastic modulus in the above-mentioned specific range. The type of ultraviolet irradiation device is not particularly limited. A high pressure mercury lamp, a metal halide lamp, etc. can be used.
【0019】本発明の透明粘着シートを板間の中間層
(中間膜)として用いることにより、各種積層体が構成
される。好ましくは、該透明粘着シートを中間層として
少なくともその片面に透明なガラス板又は合成樹脂板を
積層して積層体を作製する。例えば、該透明粘着シート
を中間層として、合成樹脂板/ガラス板、合成樹脂板/
合成樹脂板、ガラス板/ガラス板、合成樹脂板/金属
板、ガラス板/金属板等の積層体を構成することができ
る。透明な積層体あるいは片面のみが透明な板である積
層体は、良好な透明性を有する。片面に透明な板を設け
る必要のない場合、金属板/金属板等の積層体として構
成することもできる。このような積層板の作製方法に
は、種々の方法があるが、オートクレーブを用いずに積
層できる方法として、例えば、次のような方法が挙げら
れる。
Various laminates are formed by using the transparent adhesive sheet of the present invention as an intermediate layer (intermediate film) between plates. Preferably, a transparent glass plate or a synthetic resin plate is laminated on at least one surface of the transparent pressure-sensitive adhesive sheet as an intermediate layer to prepare a laminate. For example, using the transparent adhesive sheet as an intermediate layer, synthetic resin plate / glass plate, synthetic resin plate /
A laminated body such as a synthetic resin plate, a glass plate / glass plate, a synthetic resin plate / metal plate, or a glass plate / metal plate can be formed. A transparent laminate or a laminate having a transparent plate only on one side has good transparency. When it is not necessary to provide a transparent plate on one surface, it can be configured as a metal plate / metal plate laminate. There are various methods for producing such a laminated plate, and examples of the method for laminating without using an autoclave include the following methods.
【0020】先ず、積層板を構成する一方の板状体に、
予め本発明の透明粘着シートを貼り、次いで粘着剤面を
介して、他方の板状体を真空にした後にプレスして積層
する方法がある。また、先ず、積層板を構成する一方の
板状体に、予め本発明の透明粘着シートを貼り、次いで
粘着剤面を介して、他方の板状体をニップロール間で初
めて接触するようにニップロールとの間に搬入させ、ロ
ールの圧力で気泡を押し出しながら両方の板を連続的に
積層する方法がある。このようにして、実用上の使用環
境に耐え得る積層板を得ることができる。
First, one of the plate-like members constituting the laminated plate is
There is a method in which the transparent pressure-sensitive adhesive sheet of the present invention is attached in advance, and then the other plate-shaped body is evacuated via the pressure-sensitive adhesive surface and then pressed to laminate. In addition, first, the transparent pressure-sensitive adhesive sheet of the present invention is preliminarily attached to one plate-shaped body that constitutes the laminated plate, and then the other plate-shaped body is contacted with the nip rolls via the pressure-sensitive adhesive surface for the first time. There is a method in which both plates are continuously stacked while being carried in between the two and pushing out bubbles by the pressure of the roll. In this way, it is possible to obtain a laminated plate that can withstand a practical use environment.
【0021】以上、本発明の実施の形態を説明したが、
本発明は上記の実施の形態に限定されるものではなく、
本発明の要旨の範囲で種々の変形、付加等が可能であ
る。
The embodiment of the present invention has been described above.
The present invention is not limited to the above embodiment,
Various modifications and additions are possible within the scope of the present invention.
【0022】[0022]
【実施例】(実施例1)アクリル酸エステル共重合体1
00重量部に対し、有機官能基含有(メタ)アクリレー
トモノマーとして、2−イソシアネートエチルメタクリ
レート:1.0重量部、光開始剤として1−ヒドロキシ
−シクロヘキシル−フェニルケトン:0.1重量部を添
加して溶融攪拌し、透明粘着剤となし、これを厚さ10
0μmの離型フィルム(PET)間に挟んで厚み0.5
mmのシート状に成形した。これの片側の離型フィルム
(PET)側から高圧水銀ランプを積算光量で800m
J/cm2 照射させて透明粘着シートを得た。積算光量
は、オーク製作所製UV−M10のUV3tセンサーに
X19フィルターを装着して測定した。
[Example] (Example 1) Acrylic ester copolymer 1
To 100 parts by weight, 2-isocyanatoethyl methacrylate: 1.0 part by weight as an organic functional group-containing (meth) acrylate monomer, and 1-hydroxy-cyclohexyl-phenyl ketone: 0.1 part by weight as a photoinitiator were added. Melt and stir to form a transparent adhesive.
It is sandwiched between 0 μm release films (PET) and has a thickness of 0.5.
It was formed into a sheet having a size of mm. From the release film (PET) side on one side, a high-pressure mercury lamp with a cumulative light intensity of 800 m
It was irradiated with J / cm 2 to obtain a transparent adhesive sheet. The integrated light amount was measured by mounting an X19 filter on a UV3t sensor of UV-M10 manufactured by Oak Manufacturing Co., Ltd.
【0023】なお、透明粘着剤の主剤として用いた前記
アクリル酸エステル共重合体は、n−ブチルアクリレー
ト:78.4重量%、2−エチルヘキシルアクリレー
ト:19.6重量%及びアクリル酸:2.0重量%を共
重合させたもので、B型粘度計No.4ローターで測定
した130℃の溶融粘度は250000mPa・sであ
った。
The acrylic ester copolymer used as the main component of the transparent adhesive is composed of n-butyl acrylate: 78.4% by weight, 2-ethylhexyl acrylate: 19.6% by weight and acrylic acid: 2.0. B-type viscometer No. The melt viscosity at 130 ° C. measured by a 4 rotor was 250,000 mPa · s.
【0024】得られた中間膜形成用の透明粘着シートを
用いて次の方法により透明積層体を作製した。作製の際
の温度条件は、室温(20℃)下で行なった。市販のフ
ロートガラス板(厚さ3mm、幅200mm、長さ30
0mm)の一方の面に、片側の離型フィルムを剥がした
前記透明粘着シートをニップロールと駆動ロール間で、
剥がした面がフロートガラス板面に初めて接触するよう
にロール間に搬入させ、線圧力9.8N/cm、速度1
m/分で貼った後、残りの離型フィルムを剥がした。次
に、上記中間膜を形成したガラス板を中間膜を介して市
販のポリカーボネート板(厚さ2mm、幅200mm、
長さ300mm)を接触させずに向かい合わせ、2枚の
板同士がニップロールと駆動ロール間で初めて接触する
ように送り込み、ロール間に挟んで線圧力98N/c
m、速度0.5m/分で貼り合わせ、透明積層体を得
た。
A transparent laminate was produced by the following method using the obtained transparent adhesive sheet for forming an intermediate film. The temperature condition at the time of preparation was room temperature (20 ° C.). Commercially available float glass plate (thickness 3 mm, width 200 mm, length 30
(0 mm) on one surface, the transparent adhesive sheet from which the release film on one side is peeled off, between the nip roll and the drive roll,
The peeled surface was brought into contact between the rolls so that it came into contact with the float glass plate surface for the first time, and the linear pressure was 9.8 N / cm and the speed was 1
After sticking at m / min, the remaining release film was peeled off. Next, a commercially available polycarbonate plate (thickness 2 mm, width 200 mm,
(Length 300 mm) face to face without contacting each other so that the two plates contact each other for the first time between the nip roll and the drive roll, and are sandwiched between the rolls to obtain a linear pressure of 98 N / c.
and a speed of 0.5 m / min, and a transparent laminate was obtained.
【0025】(実施例2)アクリル酸エステル共重合体
100重量部に対し、有機官能基含有(メタ)アクリレ
ートモノマーとして、2−イソシアネートエチルメタク
リレート:0.2重量部、光開始剤として1−ヒドロキ
シ−シクロヘキシル−フェニルケトン:0.1重量部を
添加して溶融攪拌し、透明粘着剤となし、これを厚さ1
00μmの離型フィルム(PET)間に挟んで厚み0.
5mmのシート状に成形した。これの片側の離型フィル
ム(PET)側から高圧水銀ランプを積算光量で320
0mJ/cm2 照射させて透明粘着シートを得た。得ら
れた透明粘着シート用いて実施例1と同じ方法により透
明積層体を作製した。
Example 2 With respect to 100 parts by weight of an acrylic acid ester copolymer, 2-isocyanatoethyl methacrylate as an organic functional group-containing (meth) acrylate monomer: 0.2 parts by weight, and 1-hydroxy as a photoinitiator. -Cyclohexyl-phenyl ketone: Add 0.1 parts by weight and melt and stir to form a transparent adhesive.
It is sandwiched between 00 μm release films (PET) and has a thickness of 0.
It was formed into a 5 mm sheet. From the release film (PET) side on one side of this, a high-pressure mercury lamp with an integrated light intensity of 320
It was irradiated with 0 mJ / cm 2 to obtain a transparent adhesive sheet. A transparent laminated body was produced by the same method as in Example 1 using the obtained transparent adhesive sheet.
【0026】(実施例3)実施例2と同じ透明粘着剤を
用い、高圧水銀ランプを積算光量で1600mJ/cm
2 照射させた点を除いて実施例2と同じ方法で透明粘着
シートを得た。得られた透明粘着シート用いて実施例1
と同じ方法により透明積層体を作製した。
(Example 3) The same transparent adhesive as in Example 2 was used, and a high pressure mercury lamp was used with an integrated light amount of 1600 mJ / cm.
A transparent pressure-sensitive adhesive sheet was obtained in the same manner as in Example 2 except that the irradiation was performed. Example 1 using the obtained transparent adhesive sheet
A transparent laminate was prepared by the same method as described above.
【0027】(実施例4)アクリル酸エステル共重合体
100重量部に対し、有機官能基含有(メタ)アクリレ
ートモノマーとして、2−イソシアネートエチルメタク
リレート:0.2重量部、光開始剤として1−ヒドロキ
シ−シクロヘキシル−フェニルケトン:0.05重量部
を添加して溶融攪拌し、透明粘着剤となし、これを厚さ
100μmの離型フィルム(PET)間に挟んで厚み
0.5mmのシート状に成形した。これの片側の離型フ
ィルム(PET)側から高圧水銀ランプを積算光量で3
200mJ/cm2 照射させて透明粘着シートを得た。
得られた透明粘着シート用いて実施例1と同じ方法によ
り透明積層体を作製した。
Example 4 2-Isocyanate ethyl methacrylate: 0.2 part by weight as an organic functional group-containing (meth) acrylate monomer, and 1-hydroxy as a photoinitiator, based on 100 parts by weight of an acrylic acid ester copolymer. -Cyclohexyl-phenyl ketone: Add 0.05 parts by weight, melt and stir to form a transparent adhesive, and sandwich this between 100 μm-thick release films (PET) to form a sheet with a thickness of 0.5 mm. did. From the release film (PET) side on one side, a high-pressure mercury lamp with an integrated light amount of 3
It was irradiated with 200 mJ / cm 2 to obtain a transparent adhesive sheet.
A transparent laminated body was produced by the same method as in Example 1 using the obtained transparent adhesive sheet.
【0028】(比較例1)実施例1と同じ透明粘着剤を
用い、高圧水銀ランプを積算光量で1600mJ/cm
2 照射させた点を除いて実施例1と同じ方法で透明粘着
シートを得た。得られた透明粘着シート用いて実施例1
と同じ方法により透明積層体を作製した。
(Comparative Example 1) The same transparent adhesive as in Example 1 was used, and a high pressure mercury lamp with an integrated light amount of 1600 mJ / cm.
A transparent pressure-sensitive adhesive sheet was obtained in the same manner as in Example 1 except that two irradiations were performed. Example 1 using the obtained transparent adhesive sheet
A transparent laminate was prepared by the same method as described above.
【0029】(比較例2)実施例4と同じ透明粘着剤を
用い、高圧水銀ランプを積算光量で1600mJ/cm
2 照射させた点を除いて実施例1と同じ方法で透明粘着
シートを得た。得られた透明粘着シート用いて実施例1
と同じ方法により透明積層体を作製した。
(Comparative Example 2) The same transparent pressure-sensitive adhesive as in Example 4 was used, and a high pressure mercury lamp with an integrated light amount of 1600 mJ / cm.
A transparent pressure-sensitive adhesive sheet was obtained in the same manner as in Example 1 except that two irradiations were performed. Example 1 using the obtained transparent adhesive sheet
A transparent laminate was prepared by the same method as described above.
【0030】(試験及び評価)上記実施例及び比較例で
作製した各透明積層体の端部を露出したまま60℃×9
0%RHの環境及び−20〜80℃のヒートサイクル
(4サイクル/day)の環境に28日間保管した。保
管後の発泡、剥離及び板ズレについて観察した結果を表
1に示す。評価は、外観観察により行なった(発泡無
し:○、剥離なし:○、板ズレなし:○)。上記実施例
及び比較例で作製した各透明積層体に、積層体の反りや
割れは生じなかった。
(Test and Evaluation) 60 ° C. × 9 while leaving the end portions of the respective transparent laminates produced in the above Examples and Comparative Examples exposed.
The sample was stored in an environment of 0% RH and a heat cycle of -20 to 80 ° C (4 cycles / day) for 28 days. Table 1 shows the results of observation of foaming, peeling and plate displacement after storage. The evaluation was performed by visual observation (no foaming: ◯, no peeling: ◯, no plate displacement: ◯). The transparent laminates produced in the above Examples and Comparative Examples had no warpage or cracks in the laminates.
【0031】[0031]
【表1】 [Table 1]
【0032】表1の結果から、粘弾性特性が請求項3に
記載の貯蔵弾性率の範囲にある透明粘着シートを用いて
作成した透明積層体について、試験後も良好な外観、品
質が保たれたことが確認された。
From the results shown in Table 1, the transparent laminate prepared by using the transparent pressure-sensitive adhesive sheet having the viscoelastic property in the storage elastic modulus range described in claim 3 retains good appearance and quality after the test. It was confirmed that
【0033】[0033]
【発明の効果】本発明によれば、オートクレーブによる
高温・高圧処理を必要とすることなく、室温で合成樹脂
板やガラス板の貼り合わせを簡便に行なうことができ、
積層体の反りや割れを防止することができる。また、板
の積層加工時に板間の厚みの凹凸に馴染み、気泡のない
積層外観を得ることができ、積層後には実用上の耐久性
を確保することができる。
According to the present invention, it is possible to simply attach a synthetic resin plate or a glass plate at room temperature without the need for high temperature and high pressure treatment by an autoclave.
The laminate can be prevented from warping or cracking. Further, it is possible to adapt to the unevenness of the thickness between the plates when laminating the plates, to obtain a laminated appearance without bubbles, and to ensure practical durability after the lamination.
───────────────────────────────────────────────────── フロントページの続き Fターム(参考) 4F100 AG00A AG00C AH01B AK01A AK01C AK25B AL01B BA02 BA03 BA06 BA10A BA10C BA25B CA30B EJ05B EJ19 GB32 GB48 JD09B JG10B JK10 JL04 JL13B JN01A JN01B JN01C YY00B 4G061 AA02 AA13 BA01 BA02 CA02 CB03 CB04 CB16 CD02 CD03 CD12 CD18 CD20 DA23 DA43 4J004 AA01 AA10 AA17 AB07 BA02 4J040 DF011 DF021 FA132 JA09 JB08 JB09 KA13    ─────────────────────────────────────────────────── ─── Continued front page    F-term (reference) 4F100 AG00A AG00C AH01B AK01A                       AK01C AK25B AL01B BA02                       BA03 BA06 BA10A BA10C                       BA25B CA30B EJ05B EJ19                       GB32 GB48 JD09B JG10B                       JK10 JL04 JL13B JN01A                       JN01B JN01C YY00B                 4G061 AA02 AA13 BA01 BA02 CA02                       CB03 CB04 CB16 CD02 CD03                       CD12 CD18 CD20 DA23 DA43                 4J004 AA01 AA10 AA17 AB07 BA02                 4J040 DF011 DF021 FA132 JA09                       JB08 JB09 KA13

Claims (4)

    【特許請求の範囲】[Claims]
  1. 【請求項1】 α,β不飽和カルボン酸を含有した(メ
    タ)アクリル酸エステル系共重合体に前記不飽和カルボ
    ン酸と反応する有機官能基含有(メタ)アクリレートモ
    ノマー、光開始剤を含有したことを特徴とする透明粘着
    剤。
    1. A (meth) acrylic acid ester-based copolymer containing an α, β unsaturated carboxylic acid, an organic functional group-containing (meth) acrylate monomer that reacts with the unsaturated carboxylic acid, and a photoinitiator. A transparent adhesive characterized in that.
  2. 【請求項2】 請求項1に記載の粘着剤を厚さ0.05
    〜2mmのシート状に成形し、紫外線を照射して架橋さ
    せたことを特徴とする透明粘着シート。
    2. The adhesive according to claim 1, which has a thickness of 0.05.
    A transparent pressure-sensitive adhesive sheet, which is formed into a sheet having a size of up to 2 mm and is irradiated with ultraviolet rays to be crosslinked.
  3. 【請求項3】 前記紫外線を照射して架橋させたシート
    が下記(a)及び(b)の弾性率の範囲にあることを特
    徴とする請求項2に記載の透明粘着シート。 (a)測定温度20℃、周波数1Hzでの貯蔵弾性率
    G’(1Hz)が2×103 〜4×104 Pa。 (b)基準温度20℃、周波数10-7Hzでの貯蔵弾性
    率G’(10-7Hz)が5×101 〜2×103 Pa。
    3. The transparent pressure-sensitive adhesive sheet according to claim 2, wherein the sheet cross-linked by irradiating with the ultraviolet rays has a modulus of elasticity in the following (a) and (b). (A) Storage elastic modulus G ′ (1 Hz) at a measurement temperature of 20 ° C. and a frequency of 1 Hz is 2 × 10 3 to 4 × 10 4 Pa. (B) The storage elastic modulus G ′ (10 −7 Hz) at a reference temperature of 20 ° C. and a frequency of 10 −7 Hz is 5 × 10 1 to 2 × 10 3 Pa.
  4. 【請求項4】 請求項2又は3に記載の透明粘着シート
    を中間層として、少なくともその片面に透明なガラス板
    又は合成樹脂板を積層してなる積層体。
    4. A laminate comprising the transparent pressure-sensitive adhesive sheet according to claim 2 or 3 as an intermediate layer, and a transparent glass plate or a synthetic resin plate laminated on at least one surface thereof.
JP2002147589A 2002-05-22 2002-05-22 Transparent pressure-sensitive adhesive, transparent pressure-sensitive adhesive sheet and laminate Pending JP2003336013A (en)

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JP2006169438A (en) * 2004-12-17 2006-06-29 Mitsubishi Plastics Ind Ltd Pressure-sensitive adhesive sheet for bonding of optical element
JP2006316257A (en) * 2005-04-12 2006-11-24 Nippon Synthetic Chem Ind Co Ltd:The Pressure sensitive adhesive sheet
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JP2008037094A (en) * 2006-07-11 2008-02-21 Nippon Synthetic Chem Ind Co Ltd:The Laminate, method for producing the same, and application thereof
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JP4537012B2 (en) * 2003-03-10 2010-09-01 三菱樹脂株式会社 Designable laminate and manufacturing method thereof
JP2004268447A (en) * 2003-03-10 2004-09-30 Mitsubishi Plastics Ind Ltd Designed laminated material and its manufacturing method
JP2006169438A (en) * 2004-12-17 2006-06-29 Mitsubishi Plastics Ind Ltd Pressure-sensitive adhesive sheet for bonding of optical element
JP2006316257A (en) * 2005-04-12 2006-11-24 Nippon Synthetic Chem Ind Co Ltd:The Pressure sensitive adhesive sheet
JPWO2007029557A1 (en) * 2005-09-01 2009-03-19 三菱樹脂株式会社 Adhesive sheet
WO2007029557A1 (en) * 2005-09-01 2007-03-15 Mitsubishi Plastics, Inc. Pressure-sensitive adhesive sheet
US8470123B2 (en) 2006-02-17 2013-06-25 Lintec Corporation Pressure sensitive adhesive for sticking an electromagnetic wave-shielding film and an optically functional film, and a display panel filter element containing same
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JP2007246879A (en) * 2006-02-17 2007-09-27 Lintec Corp Adhesive for sticking electromagnetic wave-shielding film to optically functional film, and display panel filter element including the adhesive
JP2008037094A (en) * 2006-07-11 2008-02-21 Nippon Synthetic Chem Ind Co Ltd:The Laminate, method for producing the same, and application thereof
JP2008169259A (en) * 2007-01-10 2008-07-24 Mitsubishi Plastics Ind Ltd Near-infrared absorbing transparent adhesive sheet
US20120241071A1 (en) * 2009-11-06 2012-09-27 Mitsubishi Plastics, Inc. Double-sided pressure-sensitive adhesive sheet with release sheets
JP2010047020A (en) * 2009-12-01 2010-03-04 Mitsubishi Plastics Inc Designed laminated material and method of manufacturing the same
JP2016064527A (en) * 2014-09-24 2016-04-28 藤森工業株式会社 Production method and production device of curved laminate
WO2017209013A1 (en) * 2016-06-01 2017-12-07 日立化成株式会社 Photocurable resin composition for interlayer film for laminated glass, film material for interlayer film for laminated glass, and method for manufacturing laminated glass
WO2018079732A1 (en) * 2016-10-31 2018-05-03 日立化成株式会社 Laminated glass and film material for laminated-glass interlayer
WO2018078882A1 (en) * 2016-10-31 2018-05-03 日立化成株式会社 Laminated glass and production method therefor, and photocurable resin composition for laminated-glass interlayer
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