JPH03170577A - Photocurable adhesive of controlled curing shrinkage - Google Patents
Photocurable adhesive of controlled curing shrinkageInfo
- Publication number
- JPH03170577A JPH03170577A JP30907389A JP30907389A JPH03170577A JP H03170577 A JPH03170577 A JP H03170577A JP 30907389 A JP30907389 A JP 30907389A JP 30907389 A JP30907389 A JP 30907389A JP H03170577 A JPH03170577 A JP H03170577A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- adhesive
- photocurable adhesive
- curing shrinkage
- silane coupling
- 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
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 36
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 36
- 239000003822 epoxy resin Substances 0.000 claims abstract description 13
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 13
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 11
- 239000012954 diazonium Substances 0.000 claims abstract description 11
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 11
- 239000012952 cationic photoinitiator Substances 0.000 claims 1
- 239000003999 initiator Substances 0.000 abstract description 6
- -1 p-methoxybenzenediazonium hexafluorophosphate Chemical compound 0.000 abstract description 5
- 238000012663 cationic photopolymerization Methods 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 abstract description 2
- 238000001723 curing Methods 0.000 description 26
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 6
- 238000005187 foaming Methods 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 5
- 238000000016 photochemical curing Methods 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 241001147388 Uncia Species 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 238000010538 cationic polymerization reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000005304 optical glass Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000007718 adhesive strength test Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000011549 displacement method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
- H05K3/303—Surface mounted components, e.g. affixing before soldering, aligning means, spacing means
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、エポキシ系ベースレジン及びエポキシ系反応
性希釈剤からなり、耐水性に優れ、硬化時の収縮を容易
に制御出来る光硬化型接着剤に関するものであり、硬化
収縮率を２％以下に小さくもできるので、特に、精密な
位置合わせが必要とされる微小な電子・光学部品の固定
・接合に適した光硬化型接着剤に関する。Detailed Description of the Invention [Field of Industrial Application] The present invention is a photocurable adhesive that is made of an epoxy base resin and an epoxy reactive diluent, has excellent water resistance, and can easily control shrinkage during curing. The present invention relates to a photo-curable adhesive that is particularly suitable for fixing and bonding minute electronic and optical components that require precise alignment, since the curing shrinkage rate can be reduced to 2% or less.
硬化収縮率が最も小さい接着剤として知られているエボ
キシ系接着剤でも３〜５％の硬化収縮を示す。従来、こ
の点を改良するため、エポキシ樹脂をベースレジンとし
、無機系充てん剤を多量に添加した接着剤が知られ、幾
つか市販されている。しかし、これらの接着剤でも、硬
化収縮時の収縮量は２〜３％と大きく、微小な電子・光
学部品をミクロンオーダー以下の精度で接合・固定でき
る接着剤はいまだない。また、無機系充てん剤を多量に
添加した接着剤は、粘度が大きく使用しにくい。また、
スビロオルソ系樹脂を使用すると硬化時の収縮が零から
負にもなることから、この樹脂を使用した接着剤も提案
されているが、硬化し難く、紫外線を用いた硬化は極め
て難しく、実用的でない。Even epoxy adhesives, which are known as adhesives with the lowest curing shrinkage rate, exhibit curing shrinkage of 3 to 5%. Conventionally, in order to improve this point, adhesives are known in which an epoxy resin is used as a base resin and a large amount of an inorganic filler is added, and several of these are commercially available. However, even with these adhesives, the amount of shrinkage during curing is as large as 2 to 3%, and there is still no adhesive that can join and fix minute electronic and optical components with precision on the order of microns or less. Furthermore, adhesives containing large amounts of inorganic fillers have high viscosity and are difficult to use. Also,
When using subiro-ortho resin, the shrinkage during curing goes from zero to negative, so adhesives using this resin have been proposed, but they are difficult to cure and extremely difficult to cure using ultraviolet light, making them impractical. .
また、従来の接着剤は、耐久性が十分でなく、長期信頼
性が要求される電子・光学部品、例えば、通信用の電子
・光学部品用接着剤としては使用できない。Furthermore, conventional adhesives do not have sufficient durability and cannot be used as adhesives for electronic and optical components that require long-term reliability, such as electronic and optical components for communications.
本発明の目的は、上記のような欠点のない硬化収縮率制
御光硬化型接着剤を提供することにある。An object of the present invention is to provide a photocurable adhesive with controlled curing shrinkage rate that does not have the above-mentioned drawbacks.
本発明を概説すれば、本発明は硬化収縮率制御光硬化型
接着剤に関する発明であって、エボヰシ系レジンを用い
、カチオン系光重合開始剤を使用ずる光硬化型接着剤に
おいて、該エボキシ系レジンの１００重量部に対して、
ジアゾニウム塩０．０５〜０．３重量部及びシラン系カ
ップリング剤０．５〜５．０重量部を添加したことを特
徴とする。To summarize the present invention, the present invention relates to a curing shrinkage rate controlled photocurable adhesive, which uses an epoxy resin and a cationic photopolymerization initiator. For 100 parts by weight of resin,
It is characterized in that 0.05 to 0.3 parts by weight of a diazonium salt and 0.5 to 5.0 parts by weight of a silane coupling agent are added.
前記の課題を解決するために、本発明者は、光硬化時に
発泡することで硬化物の収縮をコントロールする方法に
ついて検討したところ、以前に光重合開始剤として提案
され、硬化時の発泡などの問題で現在全く使用されてい
ないジアゾニウム塩を配合することにより、光硬化時に
ジアゾニウム塩から窒素ガスを発生させ、適度に発泡さ
せることで、硬化時の収縮率を再現良く、任意の値にコ
ントロールできることを見出した。In order to solve the above problems, the present inventor investigated a method of controlling the shrinkage of the cured product by foaming during photocuring, and found that it is a method that has been previously proposed as a photopolymerization initiator and that controls foaming during curing. By incorporating diazonium salt, which is currently not used at all, the shrinkage rate during curing can be controlled to any value with good reproducibility by generating nitrogen gas from the diazonium salt and causing appropriate foaming during photocuring. I found out.
また、シラン系カップリング剤を使用することにより、
接着界面結合力を大きくでき、接着強度や耐久接着性を
向上できる。シラン系カップリング剤をブレンドして使
用する際、実用上大きな問題とされる接着時の活性化（
シラン化合物がシラノール化されて初めて接着促進硬化
を示す）と保存安定性の相反する問題も適切な配合によ
って解決できた。すなわち、オニウム塩系光重合開始剤
を用いているので、紫外線照射時に、オニウム塩から発
生するブレンステッド酸によりエボキシ基の反応が進む
と共に、シランカップリング剤が活性化（アルコキシシ
ラン基は加水分解され、シラノール基となる）され、被
着体表面の反応基（例えば、水酸基等）及びエボキシ系
レジンと結合し、接着界面結合力を大きくできる。一方
、紫外線の当たらない容器に入れ保存すると、シランは
活性化されにくいので、保存安定性も良好である。In addition, by using a silane coupling agent,
The bonding force at the adhesive interface can be increased, and the adhesive strength and durability can be improved. When blending and using silane coupling agents, activation during adhesion (
The contradictory problems of storage stability and adhesive-promoting curing (which only occurs when the silane compound is silanolized) could be resolved by appropriate formulation. In other words, since an onium salt-based photopolymerization initiator is used, upon irradiation with ultraviolet rays, the Brønsted acid generated from the onium salt progresses the reaction of the epoxy group, and the silane coupling agent is activated (the alkoxysilane group is hydrolyzed). The silanol group is bonded to the reactive group (eg, hydroxyl group, etc.) on the surface of the adherend and the epoxy resin, increasing the bonding strength at the adhesive interface. On the other hand, when stored in a container that is not exposed to ultraviolet rays, silane is less likely to be activated and has good storage stability.
本発明において用いるエボキシ系レジンとしては、一般
的に、良く知られているエポキシレジンで、特に限定さ
れない。例えば、ビスフェノールＡ型エボヰシレジン、
ビスフェノールＦ型エボキシレジン、ビスフェノールＡ
Ｄ型エボキシレジン、脂環式エボキシレジン、などの室
温で液状なものが望ましい。The epoxy resin used in the present invention is generally a well-known epoxy resin and is not particularly limited. For example, bisphenol A type evoici resin,
Bisphenol F type epoxy resin, bisphenol A
D-type epoxy resin, alicyclic epoxy resin, etc., which are liquid at room temperature, are desirable.
また、本発明においてはエボキシ系希釈剤を用いてもよ
く、その例としては、一般に、良く知られている低粘度
のエポキシ基を有する化合物、例えば、グリコール、ポ
リオール等のグリシジルエーテル、ビニルシクロヘキセ
ンジオキシドなどの脂環エポキシ化合物などを用いるこ
とができる。Further, in the present invention, an epoxy diluent may be used, and examples thereof include generally well-known compounds having a low viscosity epoxy group, such as glycidyl ethers such as glycols and polyols, and vinylcyclohexene diluents. Alicyclic epoxy compounds such as oxides can be used.
本発明において用いるカチオン系光重合開始剤としては
、鉄アレン系カチオン重合開始剤（イルガキュ了２６１
、チバガイギー社製）、トリアリルスルホニウム塩系カ
チオン重合開始剤（ｓ ｐ １ ５ ０やＳｐ１７０、
旭電化工業社製）を用いることができる。The cationic photopolymerization initiator used in the present invention is an iron allene-based cationic polymerization initiator (Irugakyurei 261
, manufactured by Ciba Geigy), triallylsulfonium salt-based cationic polymerization initiators (sp 150, Sp 170,
(manufactured by Asahi Denka Kogyo Co., Ltd.) can be used.
本発明において用いるジアゾニウム塩としては、例えば
下記の一般化学式で示される化合物を用いることができ
る。As the diazonium salt used in the present invention, for example, a compound represented by the following general chemical formula can be used.
ＡｒＮ２ Ｘ
ここで、Ａｒ：アリール基、ｘ− ： ＳｂＰｓ−Ａｓ
Ｆｓ−＋ ＰＰｓ−， ＢＦｇ−である。ArN2X where Ar: aryl group, x-: SbPs-As
Fs-+ PPs-, BFg-.
例えば、ｐ−メトキシベンゼンジアゾニウムヘキサフル
才口ホスフエートがある。For example, p-methoxybenzenediazonium hexafluorophosphate.
そのジアゾニウム塩の配合割合は、０．０５〜０．３重
量部の範囲が良い。０．０５重量部未満では、発泡によ
る収縮率の低下がほとんどない。また、０．３重量部を
越えると、硬化時の発泡が大きくなったり、多くなるた
め、機械的特性などの性能が低下し、実用上問題となる
。The blending ratio of the diazonium salt is preferably in the range of 0.05 to 0.3 parts by weight. If it is less than 0.05 parts by weight, there is almost no decrease in shrinkage rate due to foaming. Moreover, if the amount exceeds 0.3 parts by weight, foaming during curing becomes large or increases, resulting in a decrease in performance such as mechanical properties, which poses a practical problem.
本発明において用いるシラン系カップリング剤としては
、エボキシ系シランカツプリング剤、例えば、Ｔ−グリ
シドキシプロピルートリメトキシシラン（Ａ−１８７、
日本ユニカ製） β（３，４−エポキシシクロヘキシル
）一エチルトリメトキシシラン（Ａ−１８６、日本ユニ
カ製） γ−メルカプトプ口ピルートリメトキシシラ
ン（Ａ−１８９、日本ユニカ製）等を用いることができ
る。そのシラン系カップリング剤配合割合は、レジン１
００重量部に対して、０．５〜５．０重量部の範囲が良
い。０．５重量部未満では、耐久接着性が充分でない。As the silane coupling agent used in the present invention, epoxy silane coupling agents such as T-glycidoxypropyltrimethoxysilane (A-187,
(manufactured by Nippon Unica) β(3,4-epoxycyclohexyl)monoethyltrimethoxysilane (A-186, manufactured by Nippon Unica), γ-Mercaptopoletrimethoxysilane (A-189, manufactured by Nippon Unica), etc. can be used. can. The blending ratio of the silane coupling agent is 1 for resin.
0.00 parts by weight, a range of 0.5 to 5.0 parts by weight is preferable. If it is less than 0.5 part by weight, durable adhesiveness will not be sufficient.
また、５重量部を越えると、保存性が低下し易く、実用
的でない。Moreover, if it exceeds 5 parts by weight, storage stability tends to deteriorate and is not practical.
以下、本発明を実施例により更に具体的に説明するが、
本発明はこれら実施例に限定されない。Hereinafter, the present invention will be explained in more detail with reference to Examples.
The invention is not limited to these examples.
実施例１〜６、比較例１〜４
表１に、実施例、比較例の配合組或物及びそれらの主な
特性である光硬化時間、硬化収縮率、接着強度を示す。Examples 1 to 6, Comparative Examples 1 to 4 Table 1 shows the compositions of Examples and Comparative Examples and their main characteristics, such as photocuring time, curing shrinkage rate, and adhesive strength.
光硬化時間は、室温で２分間以下であり、短時間硬化で
き作業性が良い。なお、照射時の温度は発泡度合を左右
するので、高温にすることは好ましくない。また、硬化
収縮率は、自由に変えられるので、硬化収縮率を２％以
下に小さくするのは簡単である。The photocuring time is 2 minutes or less at room temperature, allowing for short curing time and good workability. Note that the temperature during irradiation affects the degree of foaming, so it is not preferable to use a high temperature. Further, since the curing shrinkage rate can be changed freely, it is easy to reduce the curing shrinkage rate to 2% or less.
接着強度は、４ ０ ｋｇ ｆ ／ｃｄ以上で、接着強
度試験時に被着体のガラスを破壊してしまう。また、８
５℃、８５％ＲＨの高温高湿雰囲気に、接着試験片を２
週間置いていても、接着強度は、４ ０ ｋｇ ｒ ／
ｃ＋＋ｆ以上を保持し、耐水性に優れている。また、
−２０℃から＋６０℃の温度サイクル試験５０サイクル
後も、接着強度は、４０ｋｇｆ／ｃＩＩ以上を保持し、
耐久性に優れている。If the adhesive strength is 40 kg f /cd or more, the glass of the adherend will be destroyed during the adhesive strength test. Also, 8
Two adhesive test pieces were placed in a high-temperature, high-humidity atmosphere at 5°C and 85% RH.
Even after leaving it for a week, the adhesive strength is 40 kgr/
It maintains C++F or higher and has excellent water resistance. Also,
Even after 50 cycles of the temperature cycle test from -20°C to +60°C, the adhesive strength remained at 40 kgf/cII or more,
Excellent durability.
なお、光硬化時間、硬化収縮率、接着強度などの評価法
は下記の通りである。The evaluation methods for photocuring time, curing shrinkage rate, adhesive strength, etc. are as follows.
光硬化時間二メタルハライドランプを使用して、約１
０ ｍＷ／ ｃｏｆの紫外線により接着部を硬化させ、
ガラス張り合せ試験片を作製した。その接着強度が１
ｋｇ ｆ ／ ｃｄ以上になった時間を硬化時間とした
。Light curing time using two metal halide lamps, approximately 1
The adhesive part is cured with ultraviolet light of 0 mW/cof,
A glass laminated test piece was prepared. Its adhesive strength is 1
The time at which the temperature reached kg f/cd or more was defined as the curing time.
硬化収縮率：硬化前後の密度を測定し、計算により求め
た。硬化前の液体の密度は振動式密度系を用い、硬化後
の密度測定は、水中置換法により求めた。Curing shrinkage rate: The density before and after curing was measured and calculated. The density of the liquid before hardening was determined using an oscillating density system, and the density after hardening was determined by an underwater displacement method.
接♀゛１強度：ＢＫ−７光学ガラスを被着体として、シ
ングルラップジョイント接着片により、せん断接着強度
を測定した。Bonding #1 Strength: Using BK-7 optical glass as an adherend, the shear bonding strength was measured using a single lap joint adhesive piece.
耐久性： ＢＫ−７光学ガラスを被着体としたラップジ
ョイント接着片を、所定時間の高温高湿又はヒートサイ
クル処理終了後、接着強度を測定して、耐久性を評価し
た。Durability: Durability was evaluated by measuring the adhesive strength of a lap joint adhesive piece using BK-7 optical glass as an adherend after completing high temperature, high humidity or heat cycle treatment for a predetermined period of time.
なお第１図は、光硬化型接着剤の硬化収縮率（％、縦軸
）とジアゾニウム塩添加量（重量部、横軸）との関係を
示すグラフである。FIG. 1 is a graph showing the relationship between the curing shrinkage rate (%, vertical axis) of a photocurable adhesive and the amount of diazonium salt added (parts by weight, horizontal axis).
本発明の硬化収縮率制御光硬化型接着剤は、エボキシ系
ベースレジン及びカチオン系光重合開始剤などからなる
配合物に、適性量のジアゾニウム塩・光照射発泡剤及び
シラン系カップリング剤を添加した配合組或物であり、
硬化時の収縮を容易に制御でき、かつ耐水性にも優れた
ものである。硬化収縮率を２％以下に小さくもできるの
で、特に、精密な位置合せが必要とされる微小な電子・
光学部品の固定・接合に適した光硬化型接着剤である。The curing shrinkage rate controlled photo-curable adhesive of the present invention is a compound consisting of an epoxy base resin, a cationic photopolymerization initiator, etc., and an appropriate amount of a diazonium salt, a photofoaming agent, and a silane coupling agent added thereto. It is a combination composition,
Shrinkage during curing can be easily controlled, and it also has excellent water resistance. Since the curing shrinkage rate can be reduced to less than 2%, it is especially suitable for microelectronic and electronic applications that require precise alignment.
A photocurable adhesive suitable for fixing and joining optical components.
第１図は、光硬化型接着剤の硬化収縮率とジアゾニウム
塩添加量との関係を示すグラフである。FIG. 1 is a graph showing the relationship between the curing shrinkage rate of a photocurable adhesive and the amount of diazonium salt added.
Claims (1)
を使用する光硬化型接着剤において、該エポキシ系レジ
ンの１００重量部に対して、ジアゾニウム塩０．０５〜
０．３重量部及びシラン系カップリング剤０．５〜５．
０重量部を添加したことを特徴とする硬化収縮率制御光
硬化型接着剤。1. In a photocurable adhesive using an epoxy resin and a cationic photoinitiator, 0.05 to 0.05 to diazonium salt is added to 100 parts by weight of the epoxy resin.
0.3 parts by weight and 0.5 to 5 parts by weight of a silane coupling agent.
A photocurable adhesive with controlled curing shrinkage rate, characterized in that 0 parts by weight is added.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30907389A JPH03170577A (en) | 1989-11-30 | 1989-11-30 | Photocurable adhesive of controlled curing shrinkage |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30907389A JPH03170577A (en) | 1989-11-30 | 1989-11-30 | Photocurable adhesive of controlled curing shrinkage |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03170577A true JPH03170577A (en) | 1991-07-24 |
Family
ID=17988556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30907389A Pending JPH03170577A (en) | 1989-11-30 | 1989-11-30 | Photocurable adhesive of controlled curing shrinkage |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03170577A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008534771A (en) * | 2005-04-04 | 2008-08-28 | ナショナル スターチ アンド ケミカル インベストメント ホールディング コーポレイション | Adhesive / sealant filled with radiation curable desiccant |
| JP2014101496A (en) * | 2012-10-25 | 2014-06-05 | Central Glass Co Ltd | Adhesive composition and adhesion method therewith, and peeling method after adhesion |
| JP2014101495A (en) * | 2012-10-25 | 2014-06-05 | Central Glass Co Ltd | Adhesive composition and adhesion method thereof, and peeling method after adhesion |
-
1989
- 1989-11-30 JP JP30907389A patent/JPH03170577A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008534771A (en) * | 2005-04-04 | 2008-08-28 | ナショナル スターチ アンド ケミカル インベストメント ホールディング コーポレイション | Adhesive / sealant filled with radiation curable desiccant |
| JP2014101496A (en) * | 2012-10-25 | 2014-06-05 | Central Glass Co Ltd | Adhesive composition and adhesion method therewith, and peeling method after adhesion |
| JP2014101495A (en) * | 2012-10-25 | 2014-06-05 | Central Glass Co Ltd | Adhesive composition and adhesion method thereof, and peeling method after adhesion |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1261783A (en) | Adhesive films of variable tack produced by irradiation of epoxide resin-acrylate film | |
| JP5919574B2 (en) | UV curable resin composition, optical component adhesive, and organic EL device sealing material | |
| IE914147A1 (en) | High performance epoxy adhesive | |
| KR101992831B1 (en) | Novel structural adhesive and use thereof | |
| JPH02158618A (en) | Curable epoxy resin composition | |
| JP2010018797A (en) | Curable composition for optical parts, adhesive agent for optical parts, and sealing agent for organic electroluminescence element | |
| JP2009098187A (en) | Adhesive for optical components | |
| JP2007169172A (en) | Method for purifying epoxy resin, adhesive for optical member and method for producing optical member | |
| JP2719616B2 (en) | Light curable precision adhesive | |
| JP2009298887A (en) | Curable composition for optical component | |
| JP6080064B2 (en) | UV curable resin composition, adhesive for optical parts, and sealing material | |
| JPH03170577A (en) | Photocurable adhesive of controlled curing shrinkage | |
| JP2010197692A (en) | Photocurable resin composition for optical member, adhesive, and touch panel | |
| JPH0657103A (en) | Photocurable resin composition | |
| JPS6051770A (en) | Optical adhesive | |
| JP2676047B2 (en) | UV curable precision adhesive | |
| JPH0673358A (en) | Refractive-index precision adhesive | |
| JP3996334B2 (en) | Photo-curable epoxy resin composition | |
| JPH04266985A (en) | Photo-setting bonding composition | |
| JP2002060484A (en) | Photocurable composition, bonding method using the same and bonded product | |
| JP2000514859A (en) | Thermosetting one-component LVA (low viscosity adhesive) adhesive system for bonding in the micro range | |
| JP2007284500A (en) | Adhesive for optical part | |
| JPS6147406A (en) | Polymerization-hardenable phosphazene compound | |
| JP4395577B2 (en) | Energy ray curable adhesive composition | |
| JPH06136098A (en) | Epoxy rein composition for electronic part |