JPS6357618A - Photocurable adhesive and bonding therewith - Google Patents
Photocurable adhesive and bonding therewithInfo
- Publication number
- JPS6357618A JPS6357618A JP20236086A JP20236086A JPS6357618A JP S6357618 A JPS6357618 A JP S6357618A JP 20236086 A JP20236086 A JP 20236086A JP 20236086 A JP20236086 A JP 20236086A JP S6357618 A JPS6357618 A JP S6357618A
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- weight
- parts
- light
- adherends
- 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.)
- Granted
Links
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 50
- 239000000853 adhesive Substances 0.000 title claims abstract description 49
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims abstract description 24
- 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 abstract description 5
- 230000001678 irradiating effect Effects 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000003999 initiator Substances 0.000 abstract description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract description 2
- 239000012965 benzophenone Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011521 glass Substances 0.000 description 11
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 6
- 239000012790 adhesive layer Substances 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
- -1 dioxolan-4-yl Chemical group 0.000 description 6
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 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
- 239000007788 liquid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-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
- 238000009835 boiling Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 150000002576 ketones Chemical class 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
- 238000002156 mixing Methods 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
- 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 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
- 150000008365 aromatic ketones Chemical class 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
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000000694 effects Effects 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
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-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
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 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
- 235000009566 rice Nutrition 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
- 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)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、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。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a novel photocurable adhesive and a bonding method using the same.
炙米夏返■
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（Ｐｏｌｙ
ｆｉｌｅ（ポリファイル）１９８５年３月号第１８紀２
４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るという欠点がある。Roasted rice summer return■ In recent years, photocurable adhesives containing active ingredients such as polyethylene glycol dimethacrylate and polyester acrylate oligomers have been developed (Poly
file (Polyfile) March 1985 issue No. 18 E2
4 pages). However, these adhesives have the disadvantage that their applications are limited because they are colored.
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。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.
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
クリ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った。Means for Solving the Problems As a result of intensive research, the inventor of the present invention found that (2-methyl-2-acetonyl-1,3-dioxolan-4-yl)methyl methacrylate and glycidyl methacrylate are used together as active ingredients. The inventors have discovered that the above object can be achieved by the following methods, and have completed the present invention.
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、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。That is, the present invention provides (2-methyl-2-acetonyl-1,3
- A photocurable adhesive containing dioxolan-4-yl) methyl methacrylate and glycidyl methacrylate as active ingredients, and the adhesive is interposed between adherends, at least one of which is transparent, and is irradiated with light. It relates to the adhesion method.
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
メタクリレート（以下、ＭＡＹ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。ＭＡＹ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。In the photocurable adhesive of the present invention, (2-methyl-2-
It is essential to use acetonyl-1,3-dioxolan-4-yl)methyl methacrylate (hereinafter referred to as MAY) and glycidyl methacrylate (hereinafter referred to as GMA) in combination as active ingredients. MAM is a compound previously disclosed by the present inventors in JP-A-60-197670, and is represented by the formula. Although MAY alone exhibits an adhesive effect when irradiated with light, the adhesive strength is not sufficient. However, M.A.M.
Furthermore, when GMA, which itself is not effective as a photocurable adhesive, is used in combination, the adhesive strength is significantly improved.
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。This fact was discovered for the first time by the present inventor.
ＭＡＹとＧＭＡとの使用割合は、広い範囲から選択でき
るが、通常ＭＡＹを５０〜９０重量％程素置対しＧＭＡ
を１０〜５０重量％程素置するのが望ましく、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、ＭＡＹが６０〜８０重量％程素置対しＧＭ
Ａが２０〜４０重Ｍ％程度である。The ratio of MAY and GMA used can be selected from a wide range, but usually about 50 to 90% by weight of MAY and GMA are used.
It is desirable that the amount of 10% to 50% by weight be present, and if it is outside this range, the adhesive strength tends to decrease. The preferred usage ratio is MAY be 60 to 80% by weight compared to GM.
A is about 20 to 40% by weight.
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−ヒドロキシシクロへキシルフェニル
ケトン、ペ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
ェトキシアセトフェノン、ベンゾインイソプロピルエー
テル、ベンゾフェ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重量部程素置好ましくは０．０５〜１重量部とする
のが適当でおる。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 ketones such as 1-hydroxycyclohexylphenyl ketone, pentyl dimethyl ketal, benzoin isobutyl ether, benzoin ethyl ether, 2,2-jethoxyacetophenone, benzoin isopropyl ether, and benzophenone. Examples thereof include type compounds and the like. 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 MAM
Usually 0.005 parts per 100 parts by weight of GMA and
A suitable amount is about 2 parts by weight, preferably 0.05 to 1 part by weight.
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、メチルエヂルケトン、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。The adhesive of the present invention is usually suitably used in a solvent-free form, but
This does not hinder the blending of solvents, and if necessary, solvents such as hydrocarbons such as toluene and xylene, ketones such as methyl edyl ketone and acetone, and esters such as ethyl acetate may be blended as appropriate.
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。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.
ＭＡＹ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。The adhesive of the present invention, which is prepared by mixing MAY and GMA, preferably adding a photopolymerization initiator, and further adding other components as necessary, is a low-viscosity liquid with high storage stability.
しかも嫌気性でおるため空気中等の酸素存在下では光が
あたっても硬化しないという特長がある。Furthermore, since it is anaerobic, it does not harden even when exposed to light in the presence of oxygen, such as in the air.
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、ポリスチレン樹脂、ポリカーボネ
ート樹脂等のプラスチック、鉄、銅、これらを含む合金
、これらのクロムメッキ材等の金属、アルミナ系セラミ
ックス等を挙げることができる。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, iron, copper, alloys containing these, metals such as chromium-plated materials, alumina ceramics, etc. can be mentioned.
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。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.
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、同種であっても異種であって
も良い。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.
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指としては、被着
物の種＠等によっても変動するが、有効成分として通常
０．０１〜０．１！ＩＦ／ ｃｉ程度とするのが適当で
ある。Examples of methods for interposing the adhesive of the present invention between adherends include brushing, spraying, pouring, and automatic coating. In addition, the amount of adhesive to be interposed varies depending on the type of adherend, etc., but the active ingredient is usually 0.01 to 0.1! It is appropriate to set it to about IF/ci.
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。ＭＡＹ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。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. The effective wavelength is approximately 270 to 500 nm. The adhesive of the present invention, in which a photopolymerization initiator is added to MAY and GMA, has extremely high sensitivity and can be sufficiently cured with light irradiation time of several tens of seconds to several minutes.
発明の効−界 本発明によれば、次の様な顕著な効果が得られる。Field of invention According to the present invention, the following remarkable effects can be obtained.
（１）接着層が無色でおり、しかも透明性が高い。(1) The adhesive layer is colorless and highly transparent.
例えばＭＡＭ７０重量％及びＧＭＡ３０重但％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。For example, when glasses are bonded together with an adhesive consisting of 70% by weight MAM and 30% by weight GMA, visible light (400~
700 nm) transmittance is 92% or more.
（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１５．５ｃｏ
ｓ／２５℃である）、嫌気性であるため明るい場所で取
扱うことができること、又接着時のはみだし部分が硬化
しないこと、臭気が殆んどないこと等により作業性が極
めて良い。(2) High sensitivity to light irradiation, high storage stability, and low viscosity liquid (for example, viscosity of 70% by weight MAM and 30% by weight GMA is 15.5 co
s/25°C), it is anaerobic so it can be handled in a bright place, the protruding parts during bonding do not harden, and there is almost no odor, so it has extremely good workability.
（３）ＭＡＹとＧＭＡとを併用したことにより接着強度
が高い。(3) Adhesive strength is high due to the combined use of MAY and GMA.
（４）接着層の耐水性、耐熱性に優れる。(4) The adhesive layer has excellent water resistance and heat resistance.
（５）無溶剤タイプとして好適に使用できるので、接着
層の硬化収縮が殆んどない。(5) Since it can be suitably used as a solvent-free type, there is almost no curing shrinkage of the adhesive layer.
（６）−液室混光硬化型でおるので、自動塗布、生産の
自動化が容易でめる。(6) - Since it is a liquid chamber mixed light curing type, automatic coating and production can be easily automated.
（７）接着層の屈折率が通常１．５前俊と高い。(7) The refractive index of the adhesive layer is usually as high as 1.5.
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。Moreover, if necessary, the above-mentioned reactive diluent can be added to further increase the amount.
夫−血一湾 以下、実施例を挙げて本発明を更に具体的に説明する。Husband - Bloody Bay Hereinafter, the present invention will be explained in more detail with reference to Examples.
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、りを調製した。Example 1 A photocurable adhesive of the present invention and a comparative photocurable adhesive were prepared according to the following formulations.
○接着剤層
ＭＡＹ ９０重量部、ＧＭＡ
１０重量部、１−ヒドロキ
シシクロ
ヘキシルフェニルケトン ０．５重量部。○Adhesive layer MAY 90 parts by weight, GMA
10 parts by weight, 0.5 parts by weight of 1-hydroxycyclohexylphenyl ketone.
０接着剤口
ＭＡＹ ８０重量部、ＧＭＡ
２０重量部、１−ヒドロキ
シシクロ
ヘキシルフェニルケトン ０．５重量部。0 Adhesive mouth MAY 80 parts by weight, GMA
20 parts by weight, 0.5 parts by weight of 1-hydroxycyclohexylphenyl ketone.
０接着剤ハ
ＭＡＭ ７０重量部、ＧＭＡ
３０重量部、ペンチルジメ
チルケタール ０．５重量部。0 Adhesive MAM 70 parts by weight, GMA
30 parts by weight, 0.5 parts by weight of pentyl dimethyl ketal.
０接着剤二
ＭＡＭ ６５重量部、ＧＭＡ
３５重量部、１−ヒドロキ
シシクロ
ヘキシルフェニルケトン ０．５重量部。0 Adhesive 2 MAM 65 parts by weight, GMA
35 parts by weight, 0.5 parts by weight of 1-hydroxycyclohexylphenyl ketone.
０接着剤ホ
ＭＡＹ 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。0 Adhesive MAY 65 parts by weight, GMA
35 parts by weight, 0.5 parts by weight of benzoin isobutyl ether.
０接着剤へ
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重足部。0 adhesive to MAM 60 parts by weight, GMA
40 parts by weight, 0.5 parts by weight of benzoin isobutyl ether.
０接着剤ト
Ｍ Ａ Ｙ ５０重量部、Ｇ
ＭＡ ５０重量部、ベンゾイ
ンイソブチルエーテル０．５重量部。0 Adhesive M AY 50 parts by weight, G
MA 50 parts by weight, benzoin isobutyl ether 0.5 parts by weight.
０接着剤チ
ＭＡＹ １００重量部、１−ヒ
ドロキシシクロ
・ヘキシルフェニルケトン ０．５重ｆｉ部。Adhesive MAY 100 parts by weight, 1-hydroxycyclohexylphenylketone 0.5 parts by weight.
０接着剤り
ＧＭＡ １００重量部、１−ヒ
ドロキシシクロ
ヘキシルフェニルケトン ０．５重量部。Adhesive GMA 100 parts by weight, 1-hydroxycyclohexylphenyl ketone 0.5 parts by weight.
実施例２
縦３０ｍ、横２５ｍ１厚ざ１ｏ履のガラス板Ａの上に、
実施例１で得た各光硬化型接着剤を流し込みにより約０
．０４’Ｊ／ｃｒｔｔの最塗布し、その上に縦３０ｍ、
横２５＃１１．厚ざ５＃のガラス板Ｂを接着面積が２５
＃Ｘ２５Ｍ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光という）
を光照射して接着を行なった。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Ｕ■光を用いたときの
光照射は１００Ｗ超高圧水銀灯（東芝■％ｒＳＨＬ−１
００ＵＶＪ 、波長２００〜６００ｎｍ）で２５ｃｍの
距離から室温下に行なった。接着部からはみ出た接着剤
は全く硬化しておらず、布で拭き取った。得られた接合
体について、ＪＩＳ Ｋ６８５２に従って圧縮せん断
接管強度及び煮沸繰返し試験を行なった。Example 2 On a glass plate A with a length of 30 m, a width of 25 m, and a thickness of 1 o,
By pouring each of the photocurable adhesives obtained in Example 1,
．． 04'J/crtt was applied, and on top of that,
Horizontal 25#11. Glass plate B with a thickness of 5 # has an adhesion area of 25
After adjusting the size to #X25M, sunlight or ultraviolet light (hereinafter referred to as UV light) is applied from the side of glass plate A under predetermined conditions.
Adhesion was performed by irradiating light. When sunlight is used as a light source, light irradiation is performed under the condition that the glass surface is perpendicular to the direct light on a clear day, and when U light is used as a light source, light irradiation is performed using a 100W ultra-high pressure mercury lamp (Toshiba ■%rSHL-1
00 UVJ, 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. The resulting joined body was subjected to compression shear joint strength and boiling cyclic tests in accordance with JIS K6852.
光照射条件及び試験結果を第１表に示す。Table 1 shows the light irradiation conditions and test results.
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
なった。Example 3 Adhesion 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.
光照射条件及び実施例２と同様に行なった試験結果を第
２表に示す。Table 2 shows the light irradiation conditions and the test results conducted in the same manner as in Example 2.
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
なった。Example 4 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 B in Example 2.
光照射条件及び実施例２と同様に行なった試験結果を第
３表に示す。Table 3 shows the light irradiation conditions and the test results conducted in the same manner as in Example 2.
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
系セラミックス板を用いた以外は、実施例２と同様にし
て、接着剤二を用いＵＶ光で２分の条件下に接着を行な
った。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, bonding was performed using adhesive No. 2 under UV light for 2 minutes. I did it.
実施例２と同様にして試験を行なったところ、圧縮せん
断接着強度は１２５ ＫＦＩ／ ｃｔＡであり、煮沸繰
返し試験は合格であった。When a test was conducted in the same manner as in Example 2, the compressive shear adhesive strength was 125 KFI/ctA, and the repeated boiling test was passed.
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
剤二を用いＵＶ光で３分の条件下に接着を行なった。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 using Agent 2 under UV light for 3 minutes.
Claims (2)
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。(1) A photocurable adhesive containing (2-methyl-2-acetonyl-1,3-dioxolan-4-yl)methyl methacrylate and glycidyl methacrylate as active ingredients.
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。(2) A photocurable adhesive containing (2-methyl-2-acetonyl-1,3-dioxolan-4-yl)methyl methacrylate and glycidyl methacrylate as active ingredients,
An adhesion method characterized by interposing the adherends, at least one of which is transparent, and irradiating them with light.
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 true JPS6357618A (en) | 1988-03-12 |
| JPH0551638B2 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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001025225A3 (en) * | 1999-09-30 | 2001-11-01 | Shell Int Research | Adducts of glycidylesters of alpha, alpha-branched carboxylic acids and acrylic 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 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001025225A3 (en) * | 1999-09-30 | 2001-11-01 | Shell Int Research | Adducts of glycidylesters of alpha, alpha-branched carboxylic acids and acrylic 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0551638B2 (en) | 1993-08-03 |
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