JPH0551638B2 - - Google Patents
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- Publication number
- JPH0551638B2 JPH0551638B2 JP61202360A JP20236086A JPH0551638B2 JP H0551638 B2 JPH0551638 B2 JP H0551638B2 JP 61202360 A JP61202360 A JP 61202360A JP 20236086 A JP20236086 A JP 20236086A JP H0551638 B2 JPH0551638 B2 JP H0551638B2
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- weight
- parts
- gma
- mam
- 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.)
- Expired - Fee Related
Links
- 230000001070 adhesive effect Effects 0.000 claims description 48
- 239000000853 adhesive Substances 0.000 claims description 47
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 24
- 239000004480 active ingredient Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- VYCAGMYQVXDIBV-UHFFFAOYSA-N [2-methyl-2-(2-oxopropyl)-1,3-dioxolan-4-yl]methyl 2-methylprop-2-enoate Chemical compound CC(=O)CC1(C)OCC(COC(=O)C(C)=C)O1 VYCAGMYQVXDIBV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011521 glass Substances 0.000 description 12
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 6
- -1 2-acetonyl-1,3-dioxolan-4-yl Chemical group 0.000 description 6
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 6
- 239000012790 adhesive layer Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- 230000001678 irradiating effect Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229940090012 bentyl Drugs 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
産業上の利用分野
本発明、新規な光硬化型接着剤及びそれを用い
る接着方法に関する。
従来の技術
近年、光硬化型接着剤としてポリエチレングリ
コールジメタルアクリレート、ポリエステルアク
リレートオリゴマー等を有効成分とするものが開
発されている（Polyfile（ポリフアイル）1985年
３月号第18〜24頁）。しかしながら、これらの接
着剤には着色しているために用途が制限されてい
るという欠点がある。
発明が解決しようとする問題点
本発明の主たる目的は、無色透明で且つ接着強
度が高い新規な光硬化型接着剤及びそれを用いる
接着方法を提供することにある。
問題点を解決するための手段
本発明者は、鋭意研究の結果、（２−メチル−
２−アセトニル−１，３−ジオキソラン−４−イ
ル）メチルメタクレートとグリシジルメタクリレ
ートとを有効成分として併用することにより上記
目的を達成できることを見出し、本発明を完成す
るに至つた。
即ち本発明は、（２−メチル−２−アセトニル
−１，３−ジオキソラン−４−イル）メチルメタ
クレートとグリシジルメタクリレートとを有効成
分とする光硬化型接着剤、並びに当該接着剤を、
少なくとも一方が透明である被着物間に介在さ
せ、光照射することを特徴とする接着方法に係
る。
本発明光硬化型接着剤においては、（２−メチ
ル−２−アセトニル−１，３−ジオキソラン−４
−イル）メチルメタクレート（以下、MAMとい
う）とグリシジルメタクリレート（以下、GMA
という）とを有効成分として併用することを必須
とする。MAMは、本発明者等が先に特開昭60−
197670号により開示した化合物であり、式
で表わされる。MAMは、単独でも光照射により
接着作用を示すが、接着強度は充分ではない。し
かし、MAMに、それ自体光硬化型接着剤として
の有効性を有しないGMAを併用するときには接
着強度が著しく向上する。かかる事実は、本発明
者により始めて見出されたものである。
MAMとGMAとの使用割合は、広い範囲から
選択できるが、通常MAMを50〜90重量％程度に
対しGMAを10〜50重量％とするのが望ましく、
この範囲外の場合には接着強度が低下する傾向に
ある。好ましい使用割合は、MAMが60〜80重量
％程度に対しGMAが20〜40重量％程度である。
本発明光硬化型接着剤においては、光重合開始
剤を添加することが望ましい。これにより、短時
間で完全に接着硬化せしめることができる。使用
し得る光重合開始剤としては、例えば１−ヒドロ
キシシクロヘキシルフエニルケトン、ベンチルジ
メチルケタール、ベンゾインイソブチルエーテ
ル、ベンゾインエチルエーテル、２，２−ジエト
キシアセトフエノン、ベンゾインイソプロピルエ
ーテル、ベンゾフエノン等の芳香族ケトン系化合
物等を挙げることができる。これらの内、接着剤
の無色透明性を損なわない点から、無色である芳
香族ケトン系化合物を用いるのが好ましい。光重
合開始剤の使用量は、MAMとGMAとの合計100
重量部に対して通常0.005〜２重量部程度、好ま
しくは0.05〜１重量部とするのが適当である。
本発明接着剤は、通常無溶剤型で好適に用いら
れるが、溶剤の配合を妨げるものではなく、必要
ならばトルエン、キシレン等の炭化水素類、メチ
ルエチルケトン、アセトン等のケトン類、酢酸エ
チル等のエステル類等の溶剤を適宜配合し得る。
また、本発明接着剤においては、更に必要に応じ
て、不飽和ポリエステル、ポリエステルアクリレ
ート、エポキシアクリレート、ウレタンアクリレ
ート等の反応性オリゴマー及び各種（メタ）アク
リレートモノマー等の反応性希釈剤等を添加配合
しても良い。
MAMとGMAを混合し、望ましくは光重合開
始剤を添加し、更に必要に応じてその他の成分を
添加してなる本発明接着剤は、保存安定性の高い
低粘度の液体である。しかも嫌気性であるため空
気中等の酸素存在下では光があたつても硬化しな
いという特長がある。
本発明接着剤により接着できる被着物として
は、各種ガラス、アクリル樹脂、ポリスレン樹
脂、ポリカーボネート樹脂等のプラスチツク、
鉄、銅、これらを含む合金、これらのクロムメツ
キ材等の金属、アルミナ系セラミツクス等を挙げ
ることができる。
本発明光硬化型接着剤を用いる接着方法は、該
接着剤を、少なくとも一方が透明である被着物間
に介在させ、光照射することにより行なわれる。
即ち、接着剤層に光エネルギーが到達する必要が
あるので被着物の少なくとも一方は透明であるこ
とが必要である。接着すべき被着物は、同種であ
つても異種であつても良い。
本発明接着剤を被着物間に介在させる方法とし
ては、ハケ塗り、スプレー、流し込み、自動塗布
等を挙げることができる。また、介在させる接着
剤の量としては、被着物の種類等によつても変動
するが、有効成分として通常0.01〜0.1ｇ／cm2程
度とするのが適当である。
本発明接着剤を被着物間に介在させることによ
り酸素との接触が遮断され、透明被着物を介して
光照射することにより短時間で硬化し被着物を好
適に接着できる。光照射は、通常太陽光、水銀
灯、キセノン灯、アーク灯、タングステン灯等の
光源を用いて行なわれる。有効波長は、270〜
500nｍ程度である。MAMとGMAとに光重合開
始剤を添加した本発明接着剤は、感度が極めて高
く、光照射時間数十秒〜数分程度で充分に接着硬
化させることができる。
発明の効果
本発明によれば、次の様な顕著な効果が得られ
る。
(1) 接着層が無色であり、しかも透明性が高い。
例えばMAM70重量％及びGMA30重量％から
なる接着剤でガラス同志を接着した場合、可視
光（400〜700nｍ）透過率は92％以上である。
(2) 光照射に対する感度が高いこと、保存安定性
が高く低粘度の液体であること（例えば
MAM70重量％及びGMA30重量％からなる場
合の粘度は05.5cp／25℃である）、嫌気性であ
るため明るい場所で取扱うことできること、又
接着時のはみだし部分が硬化しないこと、臭気
が殆どないこと等により作業性が極めて良い。
(3) MAMとGMAとを併用したことにより接着
強度が高い。
(4) 接着層の耐水性、耐熱性に優れる。
(5) 無溶剤タイプとして好適に使用できるので、
接着層の硬化収縮が殆どない。
(6) 一液室温光硬化型であるので、自動塗布、生
産の自動化が容易である。
(7) 接着層の屈折率が通常1.5前後と高い。また
必要ならば前記反応性希釈剤を添加して更に高
くすることもできる。
実施例
以下、実施例を挙げて本発明を更に具体的に説
明する。
実施例 １
下記配合により、本発明光硬化型接着剤イ〜ト
及び比較の光硬化型接着剤チ、リを調製した。
Γ接着剤イ
MAM 90重量部、
GMA 10重量部、
１−ヒドロキシシクロヘキシルフエニルケトン
0.5重量部。
Γ接着剤ロ
MAM 80重量部、
GMA 20重量部、
１−ヒドロキシシクロヘキシルフエニルケトン
0.5重量部。
Γ接着剤ハ
MAM 70重量部、
GMA 30重量部、
ベンチルジメチルケタール 0.5重量部。
Γ接着剤ニ
MAM 65重量部、
GMA 35重量部、
１−ヒドロキシシクロヘキシルフエニルケト
ン、 0.5重量部。
Γ接着剤ホ
MAM 65重量部、
GMA 35重量部、
ベンゾインイソブチルエーテル 0.5重量部。
Γ接着剤ヘ
MAM 60重量部、
GMA 40重量部、
ベンゾインイソブチルエーテル 0.5重量部。
Γ接着剤ト
MAM 50重量部、
GMA 50重量部、
ベンゾインイソブチルエーテル 0.5重量部。
Γ接着剤チ
MAM 100重量部、
１−ヒドロキシシクロヘキシルフエニルケトン
0.5重量部。
Γ接着剤リ
GMA 100重量部、
１−ヒドロキシシクロヘキシルフエニルケトン
0.5重量部。
実施例 ２
縦30mm、横25mm、厚さ10mmのガラス板Ａの上
に、実施例１で得た各硬化型接着剤を流し込みに
より約0.04ｇ／cm2の量塗布し、その上に縦30mm、
横25mm、厚さ５mmのガラス板Ｂを接着面積が25mm
×25mmになるように合せた後、所定条件でガラス
板Ａの側から太陽光又は紫外線光（以下、UVと
いう）を光照射して接着を行なつた。光源として
太陽光を用いたときの光照射は快晴時の直射光に
対してガラス面が垂直に当る条件下に、又光源と
してUV光を用いたときの光照射は100W超高圧
水銀灯（東芝(株)製「SHL−100UV」、波長200〜
600nｍ）で25cmの距離から室温下に行なつた。
接着部からはみ出た接着剤は全く硬化しておら
ず、布で拭き取つた。得られた接合体について、
JIS K6852に従つて圧縮せん断接着強度及び煮沸
繰返し試験を行なつた。
光照射条件及び試験結果を第１表に示す。
INDUSTRIAL APPLICATION FIELD The present invention relates to a novel photocurable adhesive and a bonding method using the same. BACKGROUND ART In recent years, photocurable adhesives containing polyethylene glycol dimetal acrylate, polyester acrylate oligomer, etc. as active ingredients have been developed (Polyfile, March 1985 issue, pages 18-24). However, these adhesives have the disadvantage that their applications are limited because they are colored. Problems to be Solved by the Invention The main object of the present invention is to provide a novel photocurable adhesive that is colorless and transparent and has high adhesive strength, and a bonding method using the same. Means for Solving the Problems As a result of intensive research, the present inventor discovered (2-methyl-
The inventors have discovered that the above object can be achieved by using 2-acetonyl-1,3-dioxolan-4-yl)methyl methacrylate and glycidyl methacrylate in combination as active ingredients, and have completed the present invention. That is, the present invention provides a photocurable adhesive containing (2-methyl-2-acetonyl-1,3-dioxolan-4-yl)methyl methacrylate and glycidyl methacrylate as active ingredients, and the adhesive,
It relates to an adhesion method characterized by interposing the adherends, at least one of which is transparent, between the adherends and irradiating them with light. In the photocurable adhesive of the present invention, (2-methyl-2-acetonyl-1,3-dioxolane-4
-yl) methyl methacrylate (hereinafter referred to as MAM) and glycidyl methacrylate (hereinafter referred to as GMA)
) must be used in combination as an active ingredient. MAM was developed by the present inventors in 1983-
It is a compound disclosed by No. 197670 and has the formula It is expressed as Although MAM alone exhibits an adhesive effect when exposed to light, the adhesive strength is not sufficient. However, when MAM is used in combination with GMA, which itself is not effective as a photocurable adhesive, the adhesive strength is significantly improved. This fact was discovered for the first time by the present inventor. The ratio of MAM and GMA to be used can be selected from a wide range, but it is usually desirable to use 50 to 90% by weight of MAM and 10 to 50% by weight of GMA.
Outside this range, adhesive strength tends to decrease. The preferred usage ratio is about 60 to 80% by weight of MAM and about 20 to 40% by weight of GMA. In the photocurable adhesive of the present invention, it is desirable to add a photopolymerization initiator. This allows the adhesive to be completely cured in a short time. Examples of photopolymerization initiators that can be used include aromatic compounds such as 1-hydroxycyclohexyl phenyl ketone, bentyl dimethyl ketal, benzoin isobutyl ether, benzoin ethyl ether, 2,2-diethoxyacetophenone, benzoin isopropyl ether, and benzophenone. Examples include group ketone compounds. Among these, colorless aromatic ketone compounds are preferably used from the viewpoint of not impairing the colorless transparency of the adhesive. The amount of photopolymerization initiator used is 100 in total for MAM and GMA.
It is appropriate that the amount is usually about 0.005 to 2 parts by weight, preferably 0.05 to 1 part by weight. The adhesive of the present invention is usually suitably used as a solvent-free type, but this does not hinder the combination of solvents, and if necessary, hydrocarbons such as toluene and xylene, ketones such as methyl ethyl ketone and acetone, and ethyl acetate may be used. Solvents such as esters may be appropriately blended.
In addition, in the adhesive of the present invention, reactive oligomers such as unsaturated polyester, polyester acrylate, epoxy acrylate, urethane acrylate, and reactive diluents such as various (meth)acrylate monomers may be added and blended as necessary. It's okay. The adhesive of the present invention, which is prepared by mixing MAM and GMA, preferably adding a photopolymerization initiator, and further adding other components as necessary, is a low-viscosity liquid with high storage stability. Moreover, since it is anaerobic, it does not harden even when exposed to light in the presence of oxygen such as in the air. Examples of adherends that can be bonded with the adhesive of the present invention include various types of glass, plastics such as acrylic resin, polystyrene resin, and polycarbonate resin;
Examples include iron, copper, alloys containing these, metals such as chrome-plated materials thereof, alumina ceramics, and the like. The bonding method using the photocurable adhesive of the present invention is carried out by interposing the adhesive between adherends, at least one of which is transparent, and irradiating the adherends with light.
That is, since light energy needs to reach the adhesive layer, at least one of the adherends needs to be transparent. The adherends to be bonded may be of the same type or of different types. Examples of methods for interposing the adhesive of the present invention between adherends include brushing, spraying, pouring, and automatic coating. The amount of adhesive to be interposed varies depending on the type of adherend, etc., but it is usually appropriate to use an amount of about 0.01 to 0.1 g/cm 2 as an active ingredient. By interposing the adhesive of the present invention between adherends, contact with oxygen is cut off, and by irradiating light through the transparent adherend, it cures in a short time and can suitably bond the adherends. Light irradiation is usually performed using a light source such as sunlight, a mercury lamp, a xenon lamp, an arc lamp, or a tungsten lamp. Effective wavelength is 270 ~
It is about 500nm. The adhesive of the present invention, in which a photopolymerization initiator is added to MAM and GMA, has extremely high sensitivity and can be sufficiently cured with light irradiation time of several tens of seconds to several minutes. Effects of the Invention According to the present invention, the following remarkable effects can be obtained. (1) The adhesive layer is colorless and highly transparent.
For example, when glasses are bonded together with an adhesive consisting of 70% by weight MAM and 30% by weight GMA, the visible light (400 to 700 nm) transmittance is 92% or more. (2) High sensitivity to light irradiation, high storage stability, and low viscosity liquid (e.g.
The viscosity is 05.5cp/25℃ when it is composed of 70% by weight of MAM and 30% by weight of GMA), it is anaerobic and can be handled in a bright place, the protruding part during adhesion does not harden, and there is almost no odor. etc., the workability is extremely good. (3) High adhesive strength due to combined use of MAM and GMA. (4) The adhesive layer has excellent water resistance and heat resistance. (5) It can be suitably used as a solvent-free type, so
There is almost no curing shrinkage of the adhesive layer. (6) Since it is a one-component room temperature photocuring type, automatic application and production automation are easy. (7) The refractive index of the adhesive layer is usually high, around 1.5. Moreover, if necessary, the above-mentioned reactive diluent can be added to further increase the amount. Examples Hereinafter, the present invention will be explained in more detail with reference to Examples. Example 1 Photocurable adhesives I to I of the present invention and comparative photocurable adhesives I and I were prepared using the following formulations. Γ Adhesive: 90 parts by weight of MAM, 10 parts by weight of GMA, 1-hydroxycyclohexyl phenyl ketone
0.5 parts by weight. Γ Adhesive MAM 80 parts by weight, GMA 20 parts by weight, 1-hydroxycyclohexyl phenyl ketone
0.5 parts by weight. Γ Adhesive: 70 parts by weight of MAM, 30 parts by weight of GMA, 0.5 parts by weight of bentyl dimethyl ketal. Γ adhesive: 65 parts by weight of MAM, 35 parts by weight of GMA, 0.5 parts by weight of 1-hydroxycyclohexyl phenyl ketone. 65 parts by weight of Γ adhesive HoMAM, 35 parts by weight of GMA, 0.5 parts by weight of benzoin isobutyl ether. To the Γ adhesive: 60 parts by weight of MAM, 40 parts by weight of GMA, 0.5 parts by weight of benzoin isobutyl ether. Gamma adhesive MAM 50 parts by weight, GMA 50 parts by weight, benzoin isobutyl ether 0.5 parts by weight. 100 parts by weight of Γ adhesive ChiMAM, 1-hydroxycyclohexyl phenyl ketone
0.5 parts by weight. 100 parts by weight of Γ adhesive GMA, 1-hydroxycyclohexyl phenyl ketone
0.5 parts by weight. Example 2 Each curing adhesive obtained in Example 1 was applied in an amount of about 0.04 g/cm 2 by pouring onto a glass plate A with a length of 30 mm, a width of 25 mm, and a thickness of 10 mm. ,
Glass plate B with a width of 25 mm and a thickness of 5 mm has an adhesive area of 25 mm.
After aligning the glass plates to a size of 25 mm, they were bonded by irradiating sunlight or ultraviolet light (hereinafter referred to as UV) from the side of the glass plate A under predetermined conditions. When sunlight is used as a light source, the light irradiation is performed under the condition that the glass surface is perpendicular to the direct light on a clear day, and when UV light is used as the light source, the light irradiation is performed using a 100W ultra-high pressure mercury lamp (Toshiba). "SHL-100UV" manufactured by Co., Ltd., wavelength 200~
600 nm) from a distance of 25 cm at room temperature.
The adhesive that protruded from the bonded area had not hardened at all and was wiped off with a cloth. Regarding the obtained zygote,
Compression shear adhesive strength and boiling cyclic tests were conducted in accordance with JIS K6852. Table 1 shows the light irradiation conditions and test results.
【表】
実施例 ３
実施例２においてガラス板Ｂに代えて同形状の
ステンレス鋼板を用いた以外は、実施例２と同様
にして接着を行なつた。
光照射条件及び実施例２と同様に行なつた試験
結果を第２表に示す。[Table] Example 3 Bonding was carried out in the same manner as in Example 2, except that a stainless steel plate of the same shape was used in place of glass plate B in Example 2. Table 2 shows the light irradiation conditions and the test results conducted in the same manner as in Example 2.
【表】
実施例 ４
実施例２においてガラス板Ｂに代えて同形状の
アクリル樹脂板を用いた以外は、実施例２と同様
にして接着を行なつた。
光照射条件及び実施例２と同様に行なつた試験
結果を第３表に示す。[Table] Example 4 Bonding was carried out in the same manner as in Example 2, except that an acrylic resin plate of the same shape was used in place of glass plate B in Example 2. Table 3 shows the light irradiation conditions and the test results conducted in the same manner as in Example 2.
【表】
実施例 ５
実施例２においてガラス板Ｂに代えて同形状の
アルミナ系セラミツクス板を用いた以外は、実施
例２と同様にして、接着剤ニを用いUV光で２分
の条件下に接着を行なつた。
実施例２と同様にして試験を行なつたところ、
圧縮せん断接着強度は125Kg／cm2であり、煮沸繰
返し試験は合格であつた。
実施例 ６
実施例２においてガラス板Ａに代えて同形状の
アクリル樹脂板を用い、且つガラス板Ｂに代えて
同形状のアクリル樹脂板を用いた以外は、実施例
２と同様にして、接着剤ニを用いUV光で３分の
条件下に接着を行なつた。
実施例２と同様にして試験を行なつたところ、
圧縮せん断接着強度は100Kg／cm2であり、煮沸繰
返し試験は合格であつた。[Table] Example 5 In the same manner as in Example 2, except that an alumina ceramic plate of the same shape was used in place of glass plate B in Example 2, adhesive D was used and UV light was applied for 2 minutes. I glued it on. When the test was conducted in the same manner as in Example 2,
The compressive shear adhesive strength was 125 Kg/cm 2 and passed the repeated boiling test. Example 6 Adhesion was carried out in the same manner as in Example 2, except that an acrylic resin plate of the same shape was used in place of glass plate A in Example 2, and an acrylic resin plate of the same shape was used in place of glass plate B. Adhesion was carried out under conditions of UV light for 3 minutes using agent 2. When the test was conducted in the same manner as in Example 2,
The compression shear adhesive strength was 100 Kg/cm 2 and the repeated boiling test was passed.
Claims (1)
オキソラン−４−イル）メチルメタクレートとグ
リシジルメタクリレートとを有効成分とする光硬
化型接着剤。 ２ （２−メチル−２−アセトニル−１，３−ジ
オキソラン−４−イル）メチルメタクリレートと
グリシジルメタクリレートとを有効成分とする光
硬化型接着剤を、少なくとも一方が透明である被
着物間に介在させ、光照射することを特徴とする
接着方法。[Claims] 1. A photocurable adhesive containing (2-methyl-2-acetonyl-1,3-dioxolan-4-yl)methyl methacrylate and glycidyl methacrylate as active ingredients. 2. A photocurable adhesive containing (2-methyl-2-acetonyl-1,3-dioxolan-4-yl)methyl methacrylate and glycidyl methacrylate as active ingredients is interposed between adherends, at least one of which is transparent. , an adhesion method characterized by light irradiation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20236086A JPS6357618A (en) | 1986-08-28 | 1986-08-28 | Photocurable adhesive and bonding therewith |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20236086A JPS6357618A (en) | 1986-08-28 | 1986-08-28 | Photocurable adhesive and bonding therewith |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6357618A JPS6357618A (en) | 1988-03-12 |
| JPH0551638B2 true JPH0551638B2 (en) | 1993-08-03 |
Family
ID=16456217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20236086A Granted JPS6357618A (en) | 1986-08-28 | 1986-08-28 | Photocurable adhesive and bonding therewith |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6357618A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2833701A (en) * | 1999-09-30 | 2001-05-10 | Shell Internationale Research Maatschappij B.V. | Adducts of glycidylesters of alpha, alpha-branched carboxylic acids and carboxylic acids and poly(ortho ester) as intermediate for their preparation |
| JP2008007694A (en) * | 2006-06-30 | 2008-01-17 | Sanyo Chem Ind Ltd | Photosensitive composition for adhesive agent |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59166571A (en) * | 1983-03-11 | 1984-09-19 | Nagoyashi | Preparation of coating composition curable by ultraviolet light at low temperature for electrodeposition coating |
| JPS60197670A (en) * | 1984-03-21 | 1985-10-07 | Agency Of Ind Science & Technol | Novel 1,3-dioxolane derivative compound and resin composition containing said compound as copolymer component |
-
1986
- 1986-08-28 JP JP20236086A patent/JPS6357618A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59166571A (en) * | 1983-03-11 | 1984-09-19 | Nagoyashi | Preparation of coating composition curable by ultraviolet light at low temperature for electrodeposition coating |
| JPS60197670A (en) * | 1984-03-21 | 1985-10-07 | Agency Of Ind Science & Technol | Novel 1,3-dioxolane derivative compound and resin composition containing said compound as copolymer component |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6357618A (en) | 1988-03-12 |
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