JPS62244627A - Glass laminate - Google Patents

Glass laminate

Info

Publication number
JPS62244627A
JPS62244627A JP8710786A JP8710786A JPS62244627A JP S62244627 A JPS62244627 A JP S62244627A JP 8710786 A JP8710786 A JP 8710786A JP 8710786 A JP8710786 A JP 8710786A JP S62244627 A JPS62244627 A JP S62244627A
Authority
JP
Japan
Prior art keywords
weight
parts
meth
mono
acrylate
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
JP8710786A
Other languages
Japanese (ja)
Inventor
俊司 伊藤
永太郎 福高
浮田 健吉
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Denka Co Ltd
Original Assignee
Denki Kagaku Kogyo KK
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 Denki Kagaku Kogyo KK filed Critical Denki Kagaku Kogyo KK
Priority to JP8710786A priority Critical patent/JPS62244627A/en
Publication of JPS62244627A publication Critical patent/JPS62244627A/en
Pending legal-status Critical Current

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Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。
(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明はガラス積層体に関する。特に硬化収縮率2チ以
下である、硬化物硬度がショアA35以下であるアクリ
ル系光硬化接着剤を用いて積層したガラス積層体に関す
る。
DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a glass laminate. In particular, it relates to a glass laminate laminated using an acrylic photocurable adhesive having a curing shrinkage rate of 2 inches or less and a hardness of the cured product of Shore A35 or less.

(従来の技術) ガラスの積層をブチラールフィルムを用いて製造する事
、及びエポキシ樹脂、ウレタン樹脂、シリコン樹脂等の
熱硬化樹脂を用いて製造する事は公知である。
(Prior Art) It is known to manufacture glass laminates using butyral films and thermosetting resins such as epoxy resins, urethane resins, and silicone resins.

光硬化型接着剤を用いてガラスの積層を行なう技術につ
いては、特開昭54−112917にエン/チオール型
の接着剤を用いて行なう事が示されている。また、アク
リル系光硬化型接着剤を用いてテラスの積層を行なう方
法が特開昭59−164654に示されている。
Regarding the technique of laminating glasses using a photocurable adhesive, Japanese Patent Application Laid-Open No. 112917/1983 discloses the use of an ene/thiol type adhesive. Further, a method of laminating terraces using an acrylic photocurable adhesive is disclosed in Japanese Patent Laid-Open No. 164654/1983.

(発明が解決しようとする問題点) ブチラール樹脂又は熱硬化樹脂を用いて大型のガラス同
士を積層することは、大きな加熱装置が必要で煩雑であ
る。
(Problems to be Solved by the Invention) Laminating large pieces of glass using butyral resin or thermosetting resin requires a large heating device and is complicated.

又エン/チオール系の接着剤は、柔軟な硬化物を作りや
すく空気による硬化阻害を受けにくい等の特徴があるが
、原料が入手しにくく高価である。
Furthermore, ene/thiol adhesives have the characteristics of being easy to produce a flexible cured product and being less susceptible to curing inhibition by air, but the raw materials are difficult to obtain and are expensive.

特開昭59−164654のポリエーテル又はポリエス
テルモノ(メタ)アクリレートを用いる場合、柔軟で収
縮率の低い接着系が得られるが、大型ガラスの積層用に
は収縮率が低い事が必要である為、収縮率を下げるとガ
ラスの密着性が劣り、又接着剤硬化物自体が強靭性がな
くなる傾向にある。
When using the polyether or polyester mono(meth)acrylate of JP-A-59-164654, a flexible adhesive system with a low shrinkage rate can be obtained, but a low shrinkage rate is required for laminating large glass. When the shrinkage rate is lowered, the adhesion of the glass deteriorates, and the cured adhesive itself tends to lose its toughness.

即ち大型ガラスの接着積層分野では、接着剤の硬化時の
残留応力が少なく、又ヒートサイクル時のガラスと接着
剤の熱膨張率の差を緩和できる柔軟性及び弾性を有し、
ガラスとの密着性の良好な接着剤が望まれている。
That is, in the field of adhesive lamination of large glass, adhesives have little residual stress when cured, and have flexibility and elasticity that can alleviate the difference in thermal expansion coefficient between glass and adhesive during heat cycles.
An adhesive with good adhesion to glass is desired.

(問題点を解決するだめの手段) 本発明は、硬化収縮率が2%以下であり、硬化物硬度が
ショアA35以下であり透明性の良いアクリル系光硬化
接着剤による接着層をもつガラスの積層体を提供するも
のである。
(Another Means to Solve the Problems) The present invention provides a method for producing glass that has a curing shrinkage rate of 2% or less, a hardness of the cured product of Shore A35 or less, and has an adhesive layer made of an acrylic photocurable adhesive with good transparency. The present invention provides a laminate.

本発明のガラス積層体はガラス同士を透明性の良好なア
クリル系光硬化接着剤を用いて撤庸し、積層させたもの
である、この光硬化接着剤は硬化したときその硬化物の
硬度が30以下であることが好ましい。
The glass laminate of the present invention is obtained by removing and laminating glasses using an acrylic photocurable adhesive with good transparency.When this photocurable adhesive is cured, the hardness of the cured product increases. It is preferably 30 or less.

光硬化接着剤としては、下記の(1)〜(6)より主と
してなるものが、特に好ましい。
As the photocurable adhesive, those mainly consisting of the following (1) to (6) are particularly preferable.

(1)数平均分子量が約800以上であるモノ(メタ)
アクリレート100重量部 (2)  ビニル基を含む酸性リン酸エステル1〜5重
量部 (3)  メタアクリル酸0〜10重量部(4)光重合
開始剤0.01〜5重量部(5)  シランカップリン
グ剤0〜5重量部(6)  非反応性可塑剤0〜100
重量部数平均分子量が約800以上のモノ(メタ)アク
リレートの例としては、ポリエステルモノ(メタ)アク
リレート、エポキシモノ(メタ)アクリレート等あるが
、ポリエーテルモノ(メタ)アクリレート又はウレタン
含有モノメタアクリレートが好ましい。
(1) Mono (meth) with a number average molecular weight of about 800 or more
100 parts by weight of acrylate (2) 1 to 5 parts by weight of acidic phosphoric acid ester containing a vinyl group (3) 0 to 10 parts by weight of methacrylic acid (4) 0.01 to 5 parts by weight of photopolymerization initiator (5) Silane cup Ring agent 0-5 parts by weight (6) Non-reactive plasticizer 0-100
Examples of mono(meth)acrylates having a weight part average molecular weight of about 800 or more include polyester mono(meth)acrylate and epoxy mono(meth)acrylate, but polyether mono(meth)acrylate or urethane-containing monomethacrylate is preferable.

ポリエーテルモノ(メタ)アクリレートとして°はプロ
ピレンオキサイド、エチレンオキサイド、テトラハイド
ロフラン等のホモ又はコポリマーであるポリエーテルグ
リコールのモノ(メタ)アクリレート、又はグリセリン
、サッカローズ等で分岐させたポリエーテルポリオール
のモノ(メタ)アクリレート等が挙げられる。  −ウ
レタン含有モノ(メタ)アクリレートとしては、ウレタ
ン含有モノオール、ジオール、ポリオールのモノ(メタ
)アクリレートが用いられる。この時ウレタンを生成す
る為のインシアネートとしては、黄変性を無くする為に
ヘキサメチレンジイソシアネート、インホロンジイノシ
アネート等の非黄変性イソシアネートが好ましい。
Polyether mono(meth)acrylate ° means mono(meth)acrylate of polyether glycol which is a homo or copolymer of propylene oxide, ethylene oxide, tetrahydrofuran, etc., or polyether polyol branched with glycerin, saccharose, etc. Examples include mono(meth)acrylate. - As the urethane-containing mono(meth)acrylate, mono(meth)acrylates of urethane-containing monools, diols, and polyols are used. At this time, as the incyanate for producing urethane, non-yellowing isocyanates such as hexamethylene diisocyanate and inphorone diinocyanate are preferred in order to eliminate yellowing.

ビニル基を含む酸性リン酸エステルは、下式%式% 式中、R1は ビニル基を含む有機基であり、R2はH
%R1%又は他の有機基である。R1は ビニル基、な
かでも特に(メタ)アクリル基を含むものが望ましい。
Acidic phosphoric acid ester containing a vinyl group is expressed by the following formula % formula % In the formula, R1 is an organic group containing a vinyl group, and R2 is H
%R1% or other organic group. R1 preferably contains a vinyl group, especially a (meth)acrylic group.

代表的な例として2−メタアクリロイルオキシエチルア
シッドホスフェート、又はビス(2−メタアクリロイル
オキシエチル)アシッドホスフェート等があげられる。
Typical examples include 2-methacryloyloxyethyl acid phosphate and bis(2-methacryloyloxyethyl)acid phosphate.

光重合開始剤としては、徨々公知であり例えば特開昭5
4−162798に光増感剤として述べられている様に
この分野で使われるものはいずれも使用可能である。光
重合開始剤の例としては、例えば、ベンゾフェノン、p
−メトキシベンゾフエノン、アセトフェノン、m−クロ
ルアセトン、プロピオフェノン、キサントン、ベンツイ
ン、ベンゾインメチルエーテル、ベンゾインエチルエー
テル、ベンツインイソプロビルエーテル等のベンゾイン
アルキルエーテル、ベンジルベンツアルデヒド、ベンジ
ルジメチルケタール、ナフトキノン、アントラキノン、
アゾインブチロニトリル、2,4,7.−1リニトロ−
9−フルオレノン、マラカイトグリーン等が使用できる
Photopolymerization initiators are widely known, such as those disclosed in Japanese Patent Application Laid-Open No.
Any of the photosensitizers used in this field can be used as described in No. 4-162798. Examples of photoinitiators include benzophenone, p
- benzoin alkyl ethers such as methoxybenzophenone, acetophenone, m-chloroacetone, propiophenone, xanthone, benzine, benzoin methyl ether, benzoin ethyl ether, benzine isopropyl ether, benzylbenzaldehyde, benzyl dimethyl ketal, naphthoquinone, anthraquinone,
Azoinbutyronitrile, 2,4,7. -1 Rinitro-
9-fluorenone, malachite green, etc. can be used.

シランカップリング剤はガラスの接着後の耐久性に特に
有効であり、特にビニル基又は(メタ)アクリロイル基
を含むシランカップリング剤が有効である。
Silane coupling agents are particularly effective for the durability of glass after bonding, and silane coupling agents containing vinyl groups or (meth)acryloyl groups are particularly effective.

非反応性可塑剤は、光硬化接着剤の透明性等を落さない
限り、粘度の調整、硬花物硬度の調整に使う事が出来る
Non-reactive plasticizers can be used to adjust the viscosity and hardness of photocurable adhesives, as long as they do not impair the transparency, etc. of the photocurable adhesive.

本発明のガラス積層体は例えば600mX8m以上の大
型のガラスの積層の場合でも従来の問題点のような欠陥
がなく、又、耐ヒートサイクルも良好である。
The glass laminate of the present invention has no defects such as conventional problems even when laminated with large glasses of, for example, 600 m x 8 m or more, and also has good heat cycle resistance.

(実施例) 次に実施例を用いて本発明を説明する。(Example) Next, the present invention will be explained using examples.

実施例 表1に示す配合の接着剤を調製した。この接着剤の硬化
物の物性を測定した。そして、この接着剤を用いてガラ
スとガラスを接着し、接層強度を測定した。これらの結
果を表2に示す。
EXAMPLE An adhesive having the composition shown in Table 1 was prepared. The physical properties of the cured product of this adhesive were measured. Then, this adhesive was used to bond glasses together, and the bonding strength was measured. These results are shown in Table 2.

次に表1の各々の接着剤を用いて600+++s+X工
ステル粘着テープで封じ、上端より接着剤全注入し2 
mw/−の紫外線を40分照射して硬化させた。でき上
った積層ガラスを7日間放置し、次に温度−40℃と+
80℃各2時間のヒートサイクル試験を行なった。結果
を表3に示す。
Next, use each adhesive listed in Table 1 to seal with 600+++s+X adhesive tape, and inject all of the adhesive from the top.
It was cured by irradiating it with mw/- ultraviolet light for 40 minutes. The finished laminated glass was left for 7 days, then heated to -40°C and +
A heat cycle test was conducted at 80°C for 2 hours each. The results are shown in Table 3.

表2 表3Table 2 Table 3

Claims (1)

【特許請求の範囲】 1、硬化収縮率が2%以下である、硬化物硬度がショア
A35以下である透明性のアクリル系光硬化接着剤によ
る接着層をもつガラス積層体。 2、アクリル系光硬化接着剤が、 (1)数平均分子量が約800以上であるモノ(メタ)
アクリレート100重量部 (2)ビニル基を含む酸性リン酸エステル1〜5重量部 (3)メタアクリル酸0〜10重量部 (4)光重合開始剤0.01〜5重量部 (5)シランカップリング剤0〜5重量部 (6)非反応性可塑剤0〜50重量部 上記(1)〜(6)から主としてなる事を特徴とする特
許請求の範囲第1項記載のガラス積層体。 3、モノ(メタ)アクリレートがポリエーテルモノ(メ
タ)アクリレート又はウレタン含有モノ(メタ)アクリ
レートである事を特徴とする特許請求の範囲第2項記載
のガラス積層体。
[Scope of Claims] 1. A glass laminate having an adhesive layer made of a transparent acrylic photocurable adhesive having a curing shrinkage rate of 2% or less and a hardness of the cured product of Shore A35 or less. 2. The acrylic photocurable adhesive is (1) mono (meth) having a number average molecular weight of approximately 800 or more;
100 parts by weight of acrylate (2) 1 to 5 parts by weight of acidic phosphoric acid ester containing a vinyl group (3) 0 to 10 parts by weight of methacrylic acid (4) 0.01 to 5 parts by weight of photopolymerization initiator (5) Silane cup 0 to 5 parts by weight of a ring agent (6) 0 to 50 parts by weight of a non-reactive plasticizer The glass laminate according to claim 1, characterized in that it mainly consists of the above (1) to (6). 3. The glass laminate according to claim 2, wherein the mono(meth)acrylate is polyether mono(meth)acrylate or urethane-containing mono(meth)acrylate.
JP8710786A 1986-04-17 1986-04-17 Glass laminate Pending JPS62244627A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP8710786A JPS62244627A (en) 1986-04-17 1986-04-17 Glass laminate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP8710786A JPS62244627A (en) 1986-04-17 1986-04-17 Glass laminate

Publications (1)

Publication Number Publication Date
JPS62244627A true JPS62244627A (en) 1987-10-26

Family

ID=13905720

Family Applications (1)

Application Number Title Priority Date Filing Date
JP8710786A Pending JPS62244627A (en) 1986-04-17 1986-04-17 Glass laminate

Country Status (1)

Country Link
JP (1) JPS62244627A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6706355B2 (en) * 2000-06-14 2004-03-16 Avery Dennison Corporation Protective coating for color filters
JP2012148465A (en) * 2011-01-19 2012-08-09 Jsr Corp Laminate, touch panel and composition
WO2013057957A1 (en) * 2011-10-21 2013-04-25 日本化薬株式会社 Ultraviolet ray cured resin composition, cured product, and article
WO2013069281A1 (en) * 2011-11-09 2013-05-16 日本化薬株式会社 Ultraviolet-curable resin composition, cured product, and optical member

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6706355B2 (en) * 2000-06-14 2004-03-16 Avery Dennison Corporation Protective coating for color filters
JP2012148465A (en) * 2011-01-19 2012-08-09 Jsr Corp Laminate, touch panel and composition
WO2013057957A1 (en) * 2011-10-21 2013-04-25 日本化薬株式会社 Ultraviolet ray cured resin composition, cured product, and article
CN103890028A (en) * 2011-10-21 2014-06-25 日本化药株式会社 Ultraviolet ray cured resin composition, cured product, and article
JP2017020025A (en) * 2011-10-21 2017-01-26 日本化薬株式会社 Ultraviolet-curable resin composition, cured product and article
WO2013069281A1 (en) * 2011-11-09 2013-05-16 日本化薬株式会社 Ultraviolet-curable resin composition, cured product, and optical member
JP2013100413A (en) * 2011-11-09 2013-05-23 Nippon Kayaku Co Ltd Ultraviolet-curing resin composition, cured product, and article
CN104010817A (en) * 2011-11-09 2014-08-27 日本化药株式会社 Ultraviolet-curable resin composition, cured product, and optical member
KR20140104412A (en) * 2011-11-09 2014-08-28 닛뽄 가야쿠 가부시키가이샤 Ultraviolet-curable resin composition, cured product, and optical member

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