JPS6131480A - Alpha-cyanoacrylate adhesive composition - Google Patents
Alpha-cyanoacrylate adhesive compositionInfo
- Publication number
- JPS6131480A JPS6131480A JP15313284A JP15313284A JPS6131480A JP S6131480 A JPS6131480 A JP S6131480A JP 15313284 A JP15313284 A JP 15313284A JP 15313284 A JP15313284 A JP 15313284A JP S6131480 A JPS6131480 A JP S6131480A
- Authority
- JP
- Japan
- Prior art keywords
- cyanoacrylate
- phosphoric acid
- acid
- strength
- alpha
- 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
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 title claims description 15
- 239000004830 Super Glue Substances 0.000 title description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 36
- 230000001070 adhesive effect Effects 0.000 claims abstract description 19
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 18
- 239000000853 adhesive Substances 0.000 claims abstract description 17
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims abstract description 4
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229920000137 polyphosphoric acid Polymers 0.000 claims abstract description 3
- 229940005657 pyrophosphoric acid Drugs 0.000 claims abstract description 3
- 235000011007 phosphoric acid Nutrition 0.000 claims 4
- 150000003016 phosphoric acids Chemical class 0.000 claims 1
- 238000002156 mixing Methods 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 229920001651 Cyanoacrylate Polymers 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000010960 cold rolled steel Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、金属、プラスチック、ゴム等の瞬間接着に使
用されるα−シアノアクリレート系接着剤の改質に関す
るものであシ、衝撃強度、剥離強度、剪断強度等の接着
性能が著しく優れた接着剤組成物を提供するものである
。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to the modification of α-cyanoacrylate adhesives used for instant bonding of metals, plastics, rubber, etc., and improves impact strength, The object of the present invention is to provide an adhesive composition that has extremely excellent adhesive properties such as peel strength and shear strength.
α−シアノアクリレート系接着剤の接着性を改良した例
としては、たとえば、特公昭５７−４２１０１号、特開
昭５３−３０６４３号、同５７−１０９８７６号、同５
７−１５５２７３号および同５８−１０３５６８号各公
報等に示されている。即ち、α−シアノアクリレート単
量体に対して特定の構造を有するホウ素化合物、アルデ
ヒド類、カルボン酸類または不飽和カルボン酸の共重合
体等を添加し、α−シアノアクリレートポリマーの凝集
力を高めることによって耐衝撃性を改善した例、まだ、
ジエン系ポリマーをブレンドしてα−シアノアクリレー
トポリマーに柔軟性を与えることによって剥離強度を改
善した例などである。Examples of improved adhesive properties of α-cyanoacrylate adhesives include Japanese Patent Publication Nos. 57-42101, 30643-1983, 57-109876, 5
It is shown in each publication, such as No. 7-155273 and No. 58-103568. That is, adding a boron compound having a specific structure, aldehydes, carboxylic acids, copolymers of unsaturated carboxylic acids, etc. to the α-cyanoacrylate monomer to increase the cohesive force of the α-cyanoacrylate polymer. An example of improving impact resistance by
Examples include blending diene polymers to impart flexibility to α-cyanoacrylate polymers, thereby improving peel strength.
α−シアノアクリレート系接着剤は無溶剤−液型の接着
剤であフ、被着体表面や空気中の微量水分の存在で室温
で数秒〜数十秒で重合して、金属、プラスチック、ゴム
等を接着させるという特異な性質を有しているため、工
業用や家庭用として多方面で利用されている。しかしな
がら、接着において剪断強度は良好であるものの衝撃強
度や剥離強度が不充分であり、耐久性が要求される分野
での利用には制限を受けるため、前述の如く種々の添加
剤により改善が試みられている。これらの方法によりあ
る程度の改善はみられるが充分満足できるものではなく
、また、剪断強度、衝撃強度および剥離強度を同時に改
善することば非常に困難である。即ち、各種添加剤によ
りα−シアノアクリレートのガラス転移温度を下げれば
、衝撃強度は改善されるが、剪断強度は逆に低下する傾
向にあり、剥離強度にも期待されるほどの改善はみられ
ない。捷た、添加剤によってα−シアノアクリレートポ
リマーの凝集力を増大させても界面での接着力が伴なわ
ないため、剥離強度に対しては充分な効果を発揮しない
。更に、ジエン系ポリマー等のブレンドは接着剤を不必
要に増粘させるという欠点を有している。α-Cyanoacrylate adhesive is a solvent-free liquid adhesive that polymerizes in a few seconds to tens of seconds at room temperature in the presence of trace amounts of moisture on the surface of the adherend or in the air, and can be applied to metals, plastics, rubber, etc. Because it has the unique property of adhering materials, it is used in a wide variety of industrial and household applications. However, although the shear strength of adhesion is good, the impact strength and peel strength are insufficient, which limits its use in fields where durability is required. As mentioned above, attempts have been made to improve this using various additives. It is being Although these methods provide some improvement, they are not fully satisfactory, and it is extremely difficult to simultaneously improve shear strength, impact strength, and peel strength. In other words, if the glass transition temperature of α-cyanoacrylate is lowered with various additives, the impact strength is improved, but the shear strength tends to decrease, and the expected improvement in peel strength is not observed. do not have. Even if the cohesive force of the α-cyanoacrylate polymer is increased by the use of additives, the adhesion force at the interface is not accompanied, and therefore a sufficient effect on peel strength is not exerted. Furthermore, blends such as diene-based polymers have the disadvantage of unnecessarily thickening the adhesive.
本発明の目的はα−シアノアクリレート系接着剤の本来
有している、瞬間接着性で剪断強度が良好であるという
特長を損なうことなく、衝撃強度と剥離強度を同時に改
善しようとするものである。The purpose of the present invention is to simultaneously improve impact strength and peel strength without impairing the inherent characteristics of α-cyanoacrylate adhesives, such as instant adhesiveness and good shear strength. .
本発明者等は前記従来技術の欠点を解消する目的で鋭意
研究の結果、α−シアノアクリレートに少量の無機リン
酸を添加するととによってその目的を達成した。無機リ
ン酸としては、ポリリン酸、ピロリン酸、亜リン酸、リ
ン酸等であり、その添加量はα−シアノアクリレートに
対して０．０００５〜０．１重量係、好ましくけ０．０
０１〜０．０５重量係である。この範囲をこえて少なけ
れば接着強度が不充分となり、多ければ接着速度に悪影
響を及ぼす。The inventors of the present invention have conducted extensive research aimed at solving the drawbacks of the prior art, and have achieved the objective by adding a small amount of inorganic phosphoric acid to α-cyanoacrylate. Examples of inorganic phosphoric acid include polyphosphoric acid, pyrophosphoric acid, phosphorous acid, phosphoric acid, etc., and the amount added is 0.0005 to 0.1 weight ratio relative to α-cyanoacrylate, preferably 0.0
01 to 0.05 weight ratio. If the amount exceeds this range, the adhesive strength will be insufficient, and if the amount exceeds this range, the adhesion speed will be adversely affected.
添加方法はα−シアノアクリレート単量体に直接添加し
て室温で混合するか、ヒドロキシエチルメタクリレート
のようなアクリルモノマーやジオクチルフタレートのよ
うな可塑剤に溶解させたものを添加混合してもよい。本
発明においてはこのように単に少量の無機リン酸をα−
シアノアクリレート単量体に添加するだけでその目的を
達成できるだめ接着剤を不必要に増粘させることはない
。As for the addition method, it may be added directly to the α-cyanoacrylate monomer and mixed at room temperature, or it may be added and mixed in an acrylic monomer such as hydroxyethyl methacrylate or a plasticizer such as dioctyl phthalate. In the present invention, simply adding a small amount of inorganic phosphoric acid to α-
Simply adding it to the cyanoacrylate monomer accomplishes its purpose without unnecessarily thickening the adhesive.
したがって、用途に応じて粘度を高める必要がある場合
には所定量のポリメチルメタクリレート等のポリマーを
添加溶解することによシ希望の粘度に自由に調節するこ
とも可能である。Therefore, if it is necessary to increase the viscosity depending on the application, it is possible to freely adjust the viscosity to the desired value by adding and dissolving a predetermined amount of a polymer such as polymethyl methacrylate.
無機リン酸として、リン酸、亜リン酸をα−シアノアク
リレ−）［添加した例として、特公昭４６−３７２７８
号公報があるが、これけＰＫａが０．１〜３の酸をα−
シアノアクリレートに安定剤として添加し、６０℃〜１
５０℃で加熱して滅菌処理する方法に関するものである
。また、有機リン仕合物をα−シアノアクリレートに添
加した例としては特開昭５８−６３７７１号、同５５−
１４２０６８号および特公昭５６−２５２２８号各公報
があるが、これらも接着剤の安定仕方法に関するもので
ある。As inorganic phosphoric acid, phosphoric acid and phosphorous acid are added (alpha-cyanoacrylate) [as an example of adding
There is a publication in which an acid with a PKa of 0.1 to 3 is
Added to cyanoacrylate as a stabilizer, 60℃~1
This relates to a method of sterilizing by heating at 50°C. In addition, as an example of adding an organic phosphorus compound to α-cyanoacrylate, JP-A-58-63771 and JP-A-55-
No. 142068 and Japanese Patent Publication No. 56-25228, both of which relate to methods for stabilizing adhesives.
α−シアノアクリレートに無機リン酸を少量添加するこ
とによって被着体表面との親和性が良好となり、接着破
壊面が凝集破壊を示すようになる。By adding a small amount of inorganic phosphoric acid to α-cyanoacrylate, the affinity with the adherend surface becomes good, and the adhesive failure surface shows cohesive failure.
まだ、α−シアノアクリレートポリマーの凝集力が増大
して、結果として衝撃強度、剥離強度が著しく良好とな
り、更に剪断強度にも大きな改善が認められるものであ
る。次に本発明を実施例、比較例によって更に詳細に説
明する。However, the cohesive force of the α-cyanoacrylate polymer was increased, resulting in significantly improved impact strength and peel strength, and further significant improvement was observed in shear strength. Next, the present invention will be explained in more detail with reference to Examples and Comparative Examples.
実施例１〜２０、比較例１〜５
エチル−α−シアノアクリレートまたはメチル−α−シ
アノアクリレート（いずれも市販低粘度品）を用い、表
１に示す配合組成で無機リン酸を含有する接着剤組成物
を調製し、セットタイムおよび衝撃強度を測定した。結
果を表ＩＫ示す。１だ代表的組成については、引張剪断
強度および剥離強度についても測定し、その結果を表２
に示す。Examples 1 to 20, Comparative Examples 1 to 5 Adhesives containing inorganic phosphoric acid with the formulation shown in Table 1 using ethyl-α-cyanoacrylate or methyl-α-cyanoacrylate (both commercially available low viscosity products) Compositions were prepared and set time and impact strength were measured. The results are shown in Table IK. For typical compositions, tensile shear strength and peel strength were also measured, and the results are shown in Table 2.
Shown below.
測定方法は以下の通りである。The measurement method is as follows.
〈セットタイム〉
＋ ２４０サンドペーパーで磨いた後、トリクロルエチ
レンで脱脂した５Ｓ−４１−膜構造用圧延鋼材よりなる
ブロックに接着剤を塗布し、同種のブロックを密着させ
て、２３℃、５０１ＲＨで静置し、それらが手ではがせ
なくなるまでの時間を測定してセットタイムとしだ。尚
、次に示す接着強度の測定においても鋼材の表面処理方
法は以下同様である。<Set time> + After polishing with 240 sandpaper, apply adhesive to a block made of 5S-41-rolled steel for membrane structure that has been degreased with trichloroethylene, stick blocks of the same type together, and set at 23℃ and 501RH. Let it stand, and measure the time it takes until it can no longer be removed by hand, and use it as the set time. In addition, the surface treatment method of the steel material is also the same in the following measurement of adhesive strength.
〈衝撃強度〉
ＡＳＴＭＤ９５０−５４に従って、同上の鋼材を用いて
接着し、２３℃、５０％ＲＨで２４時間放置後に衝撃強
度を測定した。<Impact Strength> According to ASTM D950-54, the same steel material as above was used for adhesion, and the impact strength was measured after being left at 23° C. and 50% RH for 24 hours.
く引張剪断強度〉
Ａ Ｓ ＴＭＤ １００２−６４に従って、厚さ１．６
咽の冷間圧延鋼板を接着し、２３℃、５０％ＲＨで２４
時間放置後に引張剪断強度を測定した。Tensile shear strength> Thickness 1.6 according to AS TMD 1002-64
Glue the cold-rolled steel plates together and heat them for 24 hours at 23°C and 50% RH.
After standing for a period of time, the tensile shear strength was measured.
〈剥離強度〉
Ｉ ８４５７８に従って、厚さ１．６ｍｍの冷間圧延鋼
板と厚さ５０μのアルミ箔を接着し、２３℃、５０％Ｒ
Ｈで２４時間放置後に剥離強度を測定した。<Peel strength> In accordance with I 84578, a cold rolled steel plate with a thickness of 1.6 mm and an aluminum foil with a thickness of 50 μm were bonded together at 23°C and 50% R.
The peel strength was measured after being left in H for 24 hours.
更に比較の為に、各実施例から無機リン酸を除いた組成
および本発明の範囲以上または以下の無機リン酸を添加
した組成についても測定しく比較例）、結果を同じく表
１１表２に示す。Furthermore, for comparison, the compositions excluding inorganic phosphoric acid from each example and the compositions adding inorganic phosphoric acid above or below the range of the present invention were also measured (comparative examples), and the results are also shown in Table 11 and Table 2. .
（以下余白）
“−７一
表２ 引張剪断強度及び剥離強度
比較例６〜１０
α−シアノアクリレート系接着剤の衝撃、剥離強度の改
善に関する従来技術について、その特許公報の明細書に
記載の組成に基づいて表３に示す配合組成で接着剤を調
製し、各接着物性を測定した。結果を表３に示す。更に
、比較の為に市販耐衝撃グレードのα−シアノアクリレ
ート接着剤についても同様に測定した。(The following is a blank space) "-7 Table 2 Tensile shear strength and peel strength comparative examples 6 to 10 Regarding the conventional technology for improving the impact and peel strength of α-cyanoacrylate adhesives, the composition described in the specification of the patent publication Adhesives were prepared with the composition shown in Table 3 based on the above, and the physical properties of each adhesive were measured.The results are shown in Table 3.Furthermore, for comparison, the same was applied to a commercially available impact grade α-cyanoacrylate adhesive. was measured.
Ｃ以下余白）
〔発明の効果〕
以上の実施例で明らかな如く、α−シアノアクリレート
単量体に単に少量の無機リン酸を添加するだけで接着に
おいて衝撃、引張剪断、剥離の全てに大幅な改善がみら
れる。逆に、比較例で示した如く、無機リン酸を含有し
ない組成および従来技術に基づく改良組成においてはそ
れらが不充分であり、特に剥離強度に大きな欠点を有し
ている。(Blank below C) [Effects of the Invention] As is clear from the above examples, simply adding a small amount of inorganic phosphoric acid to the α-cyanoacrylate monomer significantly reduces the effects of impact, tensile shear, and peeling in adhesion. Improvement is seen. On the contrary, as shown in the comparative examples, compositions that do not contain inorganic phosphoric acid and improved compositions based on the prior art are insufficient, and have major drawbacks, particularly in peel strength.
Claims (3)
無機リン酸を０．０００５〜０．１重量％添加してなる
接着剤の改良された接着剤組成物。(1) An improved adhesive composition prepared by adding 0.0005 to 0.1% by weight of one or more inorganic phosphoric acids to α-cyanoacrylate.
酸であることを特徴とする特許請求の範囲第１項記載の
接着剤組成物。(2) The adhesive composition according to claim 1, wherein the inorganic phosphoric acid is polyphosphoric acid and/or pyrophosphoric acid.
ることを特徴とする特許請求の範囲第１項記載の接着剤
組成物。(3) The adhesive composition according to claim 1, wherein the inorganic phosphoric acid is phosphoric acid and/or phosphorous acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15313284A JPS6131480A (en) | 1984-07-25 | 1984-07-25 | Alpha-cyanoacrylate adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15313284A JPS6131480A (en) | 1984-07-25 | 1984-07-25 | Alpha-cyanoacrylate adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6131480A true JPS6131480A (en) | 1986-02-13 |
| JPH0524952B2 JPH0524952B2 (en) | 1993-04-09 |
Family
ID=15555688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15313284A Granted JPS6131480A (en) | 1984-07-25 | 1984-07-25 | Alpha-cyanoacrylate adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6131480A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017075110A (en) * | 2015-10-14 | 2017-04-20 | ピアス株式会社 | Agent for promoting polymerization of 2-cyanoacrylate monomer, and method for making fiber adhere to body hair |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5863771A (en) * | 1981-09-30 | 1983-04-15 | コクタイト・コ−ポレ−シヨン | Stable cyanoacrylate adhesive composition and manufacture |
-
1984
- 1984-07-25 JP JP15313284A patent/JPS6131480A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5863771A (en) * | 1981-09-30 | 1983-04-15 | コクタイト・コ−ポレ−シヨン | Stable cyanoacrylate adhesive composition and manufacture |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017075110A (en) * | 2015-10-14 | 2017-04-20 | ピアス株式会社 | Agent for promoting polymerization of 2-cyanoacrylate monomer, and method for making fiber adhere to body hair |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0524952B2 (en) | 1993-04-09 |
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