JPS5838769A - Thixotropic ultraviolet-curing adhesive composition - Google Patents
Thixotropic ultraviolet-curing adhesive compositionInfo
- Publication number
- JPS5838769A JPS5838769A JP13751381A JP13751381A JPS5838769A JP S5838769 A JPS5838769 A JP S5838769A JP 13751381 A JP13751381 A JP 13751381A JP 13751381 A JP13751381 A JP 13751381A JP S5838769 A JPS5838769 A JP S5838769A
- Authority
- JP
- Japan
- Prior art keywords
- composition
- adhesive composition
- imidazole compound
- silica powder
- ultraviolet
- 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
Abstract
Description
【発明の詳細な説明】
本発明はチクソトロピー特性に富み、塗布作業における
垂れ、糸引き、流れ（拡がり）が改良されたチクソトロ
ピー性紫外線硬化接着剤組成物に関する０
近年、紫外線硬化性接着剤の開発動向に裏づけられるよ
うに、紫外線による化学反応の利用は複写用感光剤、デ
ィスプレー用素材、塗料、イン、キ、ＩＣ分野等におい
て盛んであり、特に、民生用機器のプリント配線基盤や
導体回路、リレー・ソケット等への利用が註目をあつめ
ている。このため、光硬化性樹脂の種類も数多く開発さ
れ、また、その用途に応じた特殊な物性を有する紫外線
硬化接着剤組成物の種類も多く提案されている。ことに
前記機器の生産においてはこれらの組成物が自動機械に
より自動的に塗布されるような特殊な物性、すなわち、
チクソトロピー性を具備することが望まれている。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a thixotropic ultraviolet curable adhesive composition that is rich in thixotropic properties and has improved sag, stringiness, and flow (spreading) during coating operations.In recent years, ultraviolet curable adhesives have been developed. As evidenced by current trends, the use of chemical reactions caused by ultraviolet light is popular in photosensitive materials for copying, display materials, paints, inks, inks, IC fields, etc., and is especially used in the printed wiring boards and conductor circuits of consumer equipment, Its use in relays, sockets, etc. is attracting attention. For this reason, many types of photocurable resins have been developed, and many types of ultraviolet curable adhesive compositions having special physical properties depending on their uses have also been proposed. Particularly in the production of said devices, these compositions have special physical properties such that they can be applied automatically by automatic machines, i.e.
It is desired to have thixotropic properties.
一般に自動機械による接着剤塗布として接着剤を先端の
細いノズルから吐出して塗布する、いわゆるディスペン
サーによる方法が良く用いられている。このディスペン
サーによる塗布は（１）高速塗布のため糸ひきかないこ
と、（２）常に安定した定量塗布ができること、（３）
被接着物に塗布ちれた接着剤が流れて広がったり、垂れ
たりしないこと、などの特性が要求される。Generally, a method using a so-called dispenser, in which the adhesive is applied by discharging the adhesive from a nozzle with a narrow tip, is often used as an adhesive application using an automatic machine. The application using this dispenser is (1) high-speed application without stringiness, (2) constant and constant amount of application, (3)
Characteristics are required, such as preventing the adhesive applied to the object from flowing, spreading, or dripping.
テクノトロピー性を具備する前述組成物として従来、無
機充填剤、例えばケイ酸マグネシュウムやケイ酸アルミ
ニウム、ベントナイト、シリカ粉末、アスベスト、マイ
カ粉などを添加してチクソトロピー性をもたせた紫外線
硬化接着剤組成物が知られている。しかしながら、この
種の組成物では無機充填剤を加えることによってチクソ
トロピー性を持たせるため：その組成物の粘度が急激に
増大して塗布作業性を極度に低下させるとともに、無機
充填剤が多く含まれるため、低粘度物質の例えば溶剤や
反応性モノマーなどで組成物粘度を調整しなければなら
ず、このため、接着剤としての物性、性能を極度に低下
させる原因ともなっている０
本発明の目的はチクソトロピー特性が付与されテテイス
ヘンサーによる塗布作業性が改良された前述の公知技術
に存する欠点をことごとく解決したチクソトロピー性紫
外線硬化接着剤組成物を提供することにある。Conventionally, the above-mentioned composition having technotropic properties is an ultraviolet curable adhesive composition which has been given thixotropic properties by adding an inorganic filler such as magnesium silicate, aluminum silicate, bentonite, silica powder, asbestos, mica powder, etc. It has been known. However, since this type of composition has thixotropic properties by adding an inorganic filler, the viscosity of the composition increases rapidly, extremely reducing coating workability, and it also contains a large amount of inorganic filler. Therefore, it is necessary to adjust the viscosity of the composition with a low-viscosity substance such as a solvent or a reactive monomer, which causes an extreme decrease in the physical properties and performance of the adhesive. It is an object of the present invention to provide a thixotropic ultraviolet curable adhesive composition which is imparted with thixotropic properties and has improved coating workability using a teteissenser, and which overcomes all the drawbacks of the above-mentioned known techniques.
前述の目的を達成するため、本発明によれば、紫外線に
よって速みゃかに硬化する（メタ）アクリレート系オリ
ゴマーまたは（メタ）アクリレート系モノマーと光増感
剤から成る紫外線硬化接着剤組成物において、前記組成
物にイミダゾール化合物とシリカ粉末の組合せよシ成る
添加剤を添加したことに婢桐１する。In order to achieve the above object, the present invention provides an ultraviolet curable adhesive composition comprising a (meth)acrylate oligomer or a (meth)acrylate monomer that is rapidly cured by ultraviolet rays and a photosensitizer. The present invention is based on the fact that an additive consisting of a combination of an imidazole compound and silica powder is added to the composition.
紫外線硬化性ベース樹脂となる（メタ）アクリレート系
オリゴマーまたは（メタ）アクリレート系モノマーの代
表的なものとして、ネオペンチルグリコールジアクリレ
ート、ジエチレングリコールジアクリレート、テトラヒ
ドロフルフリルアクリレート、テトラエチレングリコー
ルジアクリレート、ポリエチレングリコールジアクリレ
ート、２−２ビス（４−アクリロキシジェトキシフェニ
ル）プロパン、エポキシアクリレートなどが挙げられ、
また光増感剤として、ベンゾインエチルエーテル、ペン
ツインメチルエーテル、ペンゾインイノプロビルエーテ
ル、アントラキノン等のカルボニル化合物、ジフェニル
スルフィト、シヘンゾイルスルフイド、テトラメチルチ
ウラムスルフィド等の硫黄化合物、その他アントラセン
化合物、・・ロゲン化炭化水素等があげられる。また本
発明の添加剤となるイミダゾール化合物は２−メチルイ
ミダゾール、２−エチル−４−メチルイミダゾール％
２−フェニルイミダゾール、２−ウンデシルイミダゾー
ル、２−エチルイミダゾール、２−一＼ブタデシルイミ
ダゾール、２−フェニルイミダゾール、２−エチル−４
−メチルイミダシリン、２−一＼ブタデシルイミダシリ
ン、２−４−ジメチルイミグゾール等であり、その他イ
ミダゾール誘導体であってもかまわない。これらのイミ
ダゾール化合物の中には公知の前記紫外線硬化接着剤組
成物に不溶のものもあるが、この場合、アルコール、ア
セトン、ベンゼン等の溶剤に溶解して添加することがで
き、また加熱して溶融した後添加しても良い。Typical examples of (meth)acrylate oligomers or (meth)acrylate monomers used as UV-curable base resins include neopentyl glycol diacrylate, diethylene glycol diacrylate, tetrahydrofurfuryl acrylate, tetraethylene glycol diacrylate, and polyethylene glycol. Diacrylate, 2-2bis(4-acryloxyjethoxyphenyl)propane, epoxy acrylate, etc.
In addition, as photosensitizers, carbonyl compounds such as benzoin ethyl ether, pentuin methyl ether, penzoin inoprobyl ether, anthraquinone, sulfur compounds such as diphenyl sulfite, cyhenzoyl sulfide, tetramethylthiuram sulfide, etc. Examples include anthracene compounds, logenated hydrocarbons, etc. In addition, the imidazole compound used as an additive in the present invention is 2-methylimidazole, 2-ethyl-4-methylimidazole%
2-phenylimidazole, 2-undecylimidazole, 2-ethylimidazole, 2-1\butadecylimidazole, 2-phenylimidazole, 2-ethyl-4
-methylimidacillin, 2-1\butadecylimidacillin, 2-4-dimethylimidacillin, and other imidazole derivatives. Some of these imidazole compounds are insoluble in the known ultraviolet curable adhesive compositions, but in this case, they can be dissolved in a solvent such as alcohol, acetone, benzene, etc., or added by heating. It may be added after melting.
本発明者等は前記公知の紫外線硬化接着剤組成物に単に
前記イミダゾール化合物のみを加えても本発明の目的で
あるチクソトロピー性は全く得られず、またシリカ粉末
のみを前記接着剤組成物に加えても増粘が大きく、目的
とするチクソトロピー性は得られないことを種々実験で
確認した。また、他３の無機粉末、ケイ酸マグネシウム
、ケイ酸アルミニウム、ベントナイト、アスベスト粉、
マイカ粉、タルクなどとイミダゾール化合物の組合せに
おいても本発明のごとき特異なチクソトロピー性は得ら
れない。このようにして本発明は公知の紫外線硬化接着
剤組成物にイミダゾール化合物とシリカ粉末の組合せか
らなる添加剤を加えることにより所望の効果が得られる
ものであるが、この理由はシリカ粉末の表面末端にある
一〇Ｈ基とイミダゾール化合物とが水素結合し、サスペ
ンションの中、シリカ粉末間で一種の構造を形成するた
めと考えられる。また紫外線硬化接着剤組成物１００重
量部にイミダゾール化合物とシリカ粉末からなる添加剤
０．１〜１５重量部加えたものが最も効果が大きい。こ
の添加剤が少なくなると、本発明の目的とする塗布作業
における適当なチクノドロビー性が充分に得られず、ま
た多くなった場合は接着剤として硬化後の物性、すなわ
ち光の照射が充分に行なわれず接着強度が低下してくる
０また添加剤となるイミダゾール化合物とシリカ粉末は
前者が０．１〜１０ Ｘ 、後者が９０〜９９．９％の
範囲で添加することが最もよく、イミダゾール化合物が
少なくなるとシリカ粉末による増粘が大きくなり、イミ
ダゾール化合物とシリカ粉末の組合せによる効果が少な
くなる０
またイミダゾール化合物が多くなると硬化物の硬さが低
下し充分な強度が得られない０さらに本発明の組成物に
一般に知られる重合抑制剤を添加しても良い。The present inventors discovered that simply adding only the imidazole compound to the known UV-curable adhesive composition did not provide the thixotropic properties that are the object of the present invention, and that adding only silica powder to the adhesive composition It was confirmed through various experiments that the desired thixotropy could not be obtained even if the viscosity increased significantly even if In addition, three other inorganic powders, magnesium silicate, aluminum silicate, bentonite, asbestos powder,
Even in combinations of mica powder, talc, etc. and imidazole compounds, the unique thixotropic properties of the present invention cannot be obtained. In this way, the present invention provides a desired effect by adding an additive consisting of a combination of an imidazole compound and silica powder to a known ultraviolet curable adhesive composition. This is thought to be due to hydrogen bonding between the 10H group in the imidazole compound and the formation of a type of structure between the silica powders in the suspension. Moreover, the most effective is obtained by adding 0.1 to 15 parts by weight of an additive consisting of an imidazole compound and silica powder to 100 parts by weight of the ultraviolet curable adhesive composition. If the amount of this additive is too low, it will not be possible to sufficiently obtain the appropriate tingling properties in the coating work that is the objective of the present invention, and if it is too large, the physical properties of the adhesive after curing, that is, the irradiation with light, will not be sufficient. It is best to add the imidazole compound and silica powder as additives in the range of 0.1 to 10% and the latter in the range of 90 to 99.9%. If the amount of the imidazole compound increases, the hardness of the cured product decreases and sufficient strength cannot be obtained.Furthermore, the composition of the present invention Generally known polymerization inhibitors may be added to the product.
以上のように本発明は一般に知られる紫外線硬化接着剤
組成物にイミダゾール化合物とシリカ粉末からなる添加
剤を添加することにより、良好なチクソトロピー特性を
呈し、本発明の目的を達成し得るものでおる。As described above, the present invention exhibits good thixotropic properties and achieves the objects of the present invention by adding additives consisting of an imidazole compound and silica powder to a generally known ultraviolet curable adhesive composition. .
実施例（１）
表１に示すような各種メタアクリレート系オリゴマーま
たはモノマー１００２にベンゾインエチルエーテル２？
を添加したものを基本組成物（１）とし、−該組成物（
１）に１−ベンジル−２−メチルイミダゾール０．４ｆ
を添加したものを組成物（２）とした。また組成物（１
）にシリカ粉末８ｆ添加したものを組成物（３）とし、
組成物（１）に１−ベンジル−２−メチルイミダゾール
０．４ｆ、シリカ粉末８２添加したものを本発明組成物
としてこれらの組成物のそれぞれについて粘度ならびに
チクソトロピー性を測定した。なおチクソトロピー性は
チクソトロピツク係数として表わした。粘度測定は東京
計器（彬製ＢＨ型回転粘度計翫７０、−ターを使用し５
℃工測測定た。チクソトロビツク係数は２ｒｐｍ／２Ｏ
ｒｐｍ比で求め、粘度は２Ｏｒｐｍ時で示した。Example (1) Benzoin ethyl ether 2?
is added to the basic composition (1), - the composition (
1) to 1-benzyl-2-methylimidazole 0.4f
The composition to which was added was designated as composition (2). Also, the composition (1
) to which 8f of silica powder was added is referred to as composition (3),
Composition (1) to which 0.4 f of 1-benzyl-2-methylimidazole and 82 g of silica powder were added was used as a composition of the present invention, and the viscosity and thixotropy of each of these compositions were measured. The thixotropy was expressed as a thixotropic coefficient. The viscosity was measured using Tokyo Keiki (BH type rotational viscometer 70, made by Akira).
℃ engineering measurements were taken. Thixotrovic coefficient is 2 rpm/2O
It was determined by the rpm ratio, and the viscosity was shown at 2 Orpm.
実施例（２）
２・２ビス（４−アクリロキシジェトキシフェニル）フ
ロパン１００ＰＫベンゾインエチルエーテル２９を添加
した組成物（実施例１のモノマー翫６組成物１と同じ）
に、表２に示すような各種イミダゾール化合物０．８ｆ
とシリカ粉末８ｖを組合せた添加剤を添加してそれぞ
れの粘度ならびにチクソトロピツク係数を実施例１と同
様にして求めた。Example (2) Composition to which 2.2-bis(4-acryloxyjethoxyphenyl)furopane 100PK benzoin ethyl ether 29 was added (same as Monomer 6 Composition 1 of Example 1)
0.8f of various imidazole compounds as shown in Table 2.
The viscosity and thixotropic coefficient of each additive were determined in the same manner as in Example 1, by adding an additive consisting of silica powder and 8 vol of silica powder.
実施例（３）
実施例１に示したそれぞれの組成物のうちシリカ粉末の
みを添加した組成物とイミダゾール化合物とシリカ粉末
の組合せによる添加剤を添加した組成物についてディス
ペンサーより吐出する吐出性と流動性を測定した０なお
、吐出性はノズル径０．５醪エアー圧５ ｋｆ／ ／
ＣＪの条件で組成物５■吐出する時間を測定することに
より評価した。また流動性は各組成物をガラス板上に滴
下し、その直後の直径と５分後の直径の差を測定した０
表２
表３
以上の実施例から明らかなように本発明の目的とする低
粘度を保ちながらチクソトロピー性に持たせることにお
いて、公知の紫外線硬化接着剤組成物にイミダゾール化
合物とシリカ粉末からなる添加剤金加えることにより従
来に見られなかった特異な性状が得られるものである。Example (3) Out of the respective compositions shown in Example 1, the ejectability and fluidity of the composition added with only silica powder and the composition added with an additive of a combination of an imidazole compound and silica powder from a dispenser In addition, the discharge performance was measured at a nozzle diameter of 0.5 and an air pressure of 5 kf/ /
Evaluation was made by measuring the time taken to discharge Composition 5 under CJ conditions. Fluidity was determined by dropping each composition onto a glass plate and measuring the difference in diameter immediately after and 5 minutes later.
Table 2 Table 3 As is clear from the above examples, additives consisting of an imidazole compound and silica powder were added to a known ultraviolet curable adhesive composition to provide thixotropic properties while maintaining the low viscosity that is the objective of the present invention. By adding gold, unique properties not seen before can be obtained.
すなわち、シリカ粉末ならびにイミダゾール化合物のそ
れぞれの添加割合および前記公知の紫外線硬化接着剤組
成物に対する添加量は用途に応じて適宜調整することに
より粘度、チクソトロピー性を自由に調整することが可
能である。例えばディスペンサーで塗布する場合では粘
度６５０〜１１００ポイズ（′２５℃における）チクソ
トロピツク係数６〜８の性状を有するものが良く、短時
間で吐出が可能であるばかりでなく糸引きならびに定量
塗布や塗布後の広がり、垂れが生じないなど種々の特徴
を有するものであり今後径々自動化が進む中にあって省
力化、品質向上など企業的価値大なるものがある。That is, the viscosity and thixotropy can be freely adjusted by adjusting the respective addition ratios of silica powder and imidazole compound and the amounts added to the above-mentioned known ultraviolet curable adhesive composition depending on the application. For example, when applying with a dispenser, a material with a viscosity of 650 to 1100 poise (at '25°C) and a thixotropic coefficient of 6 to 8 is preferable, and not only can it be dispensed in a short time, but it can also be used for stringing, fixed amount application, and after application. It has various characteristics such as spreading and no sag, and as automation continues to progress in the future, it will have great corporate value such as labor saving and quality improvement.
Claims (2)
リレート系オリゴマーまたは（メタ）アクリレート系モ
ノマーと光増感剤とから成る紫外線硬化性樹脂組成物に
おいて、前記組成物にイミダゾール化合物とシリカ粉末
の組合せより成る添加剤を添加したことを特徴とするチ
クソトロピー性紫外線硬化接着剤組成物０(1) In an ultraviolet curable resin composition comprising a (meth)acrylate oligomer or (meth)acrylate monomer and a photosensitizer that is rapidly cured by ultraviolet rays, an imidazole compound and a silica powder are added to the composition. Thixotropic ultraviolet curing adhesive composition 0 characterized by adding a combination of additives
タ）アクリレート系モノマーと光増感剤とから成る接着
剤組成物１００重量部に対しイミダゾール化合物とシリ
カ粉末から成る添加剤０１〜１５重量部加えることを特
徴とする特許請求範囲第１項記載のチクソトロピー性紫
外線硬化接着剤組成物０(2) 01 to 15 parts by weight of an additive consisting of an imidazole compound and silica powder per 100 parts by weight of an adhesive composition consisting of a (meth)acrylate oligomer or a (meth)acrylate monomer and a photosensitizer. The thixotropic ultraviolet curable adhesive composition 0 according to claim 1, characterized in that
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13751381A JPS5838769A (en) | 1981-08-31 | 1981-08-31 | Thixotropic ultraviolet-curing adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13751381A JPS5838769A (en) | 1981-08-31 | 1981-08-31 | Thixotropic ultraviolet-curing adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5838769A true JPS5838769A (en) | 1983-03-07 |
| JPH0160072B2 JPH0160072B2 (en) | 1989-12-20 |
Family
ID=15200418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13751381A Granted JPS5838769A (en) | 1981-08-31 | 1981-08-31 | Thixotropic ultraviolet-curing adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5838769A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01232735A (en) * | 1988-03-11 | 1989-09-18 | Matsushita Electric Ind Co Ltd | Semiconductor device |
| JPH0250378A (en) * | 1988-08-11 | 1990-02-20 | Kemitetsuku Kk | Method for providing sealing member to magnetic disk driving housing |
| US4963002A (en) * | 1988-03-07 | 1990-10-16 | Sharp Kabushiki Kaisha | Connection construction and method of manufacturing the same |
| JPH03152178A (en) * | 1989-11-09 | 1991-06-28 | Hayakawa Rubber Co Ltd | Tacky composition of active energetic ray-curing type |
| JP2001247608A (en) * | 2000-03-09 | 2001-09-11 | Citizen Watch Co Ltd | Protective agent |
| JP2007315699A (en) * | 2006-05-26 | 2007-12-06 | Asahi Glass Co Ltd | Furnace interior heating method and furnace interior heating device |
| JP2011052033A (en) * | 2009-08-31 | 2011-03-17 | Hitachi Media Electoronics Co Ltd | Photocurable adhesive, optical pickup device, and production method therefor |
| JP2012212502A (en) * | 2012-06-11 | 2012-11-01 | Nhk Spring Co Ltd | Head suspension and piezoelectric element adhering method |
-
1981
- 1981-08-31 JP JP13751381A patent/JPS5838769A/en active Granted
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4963002A (en) * | 1988-03-07 | 1990-10-16 | Sharp Kabushiki Kaisha | Connection construction and method of manufacturing the same |
| JPH01232735A (en) * | 1988-03-11 | 1989-09-18 | Matsushita Electric Ind Co Ltd | Semiconductor device |
| JPH0250378A (en) * | 1988-08-11 | 1990-02-20 | Kemitetsuku Kk | Method for providing sealing member to magnetic disk driving housing |
| JPH03152178A (en) * | 1989-11-09 | 1991-06-28 | Hayakawa Rubber Co Ltd | Tacky composition of active energetic ray-curing type |
| JP2001247608A (en) * | 2000-03-09 | 2001-09-11 | Citizen Watch Co Ltd | Protective agent |
| JP2007315699A (en) * | 2006-05-26 | 2007-12-06 | Asahi Glass Co Ltd | Furnace interior heating method and furnace interior heating device |
| JP2011052033A (en) * | 2009-08-31 | 2011-03-17 | Hitachi Media Electoronics Co Ltd | Photocurable adhesive, optical pickup device, and production method therefor |
| JP2012212502A (en) * | 2012-06-11 | 2012-11-01 | Nhk Spring Co Ltd | Head suspension and piezoelectric element adhering method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0160072B2 (en) | 1989-12-20 |
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