JPH0147504B2 - - Google Patents
Info
- Publication number
- JPH0147504B2 JPH0147504B2 JP14738280A JP14738280A JPH0147504B2 JP H0147504 B2 JPH0147504 B2 JP H0147504B2 JP 14738280 A JP14738280 A JP 14738280A JP 14738280 A JP14738280 A JP 14738280A JP H0147504 B2 JPH0147504 B2 JP H0147504B2
- Authority
- JP
- Japan
- Prior art keywords
- diketone
- cyanoacrylate
- present
- adhesive
- composition
- 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
Links
- 239000000203 mixture Substances 0.000 claims description 24
- 239000000853 adhesive Substances 0.000 claims description 20
- 230000001070 adhesive effect Effects 0.000 claims description 20
- 125000005594 diketone group Chemical group 0.000 claims description 19
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 16
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical group CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 6
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 claims description 2
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 claims description 2
- STGAELBFKJDACH-UHFFFAOYSA-N 2-fluoro-1-thiophen-2-ylbutane-1,3-dione Chemical compound CC(=O)C(F)C(=O)C1=CC=CS1 STGAELBFKJDACH-UHFFFAOYSA-N 0.000 claims description 2
- OWLPCALGCHDBCN-UHFFFAOYSA-N 4,4,4-trifluoro-1-(furan-2-yl)butane-1,3-dione Chemical compound FC(F)(F)C(=O)CC(=O)C1=CC=CO1 OWLPCALGCHDBCN-UHFFFAOYSA-N 0.000 claims description 2
- VVXLFFIFNVKFBD-UHFFFAOYSA-N 4,4,4-trifluoro-1-phenylbutane-1,3-dione Chemical compound FC(F)(F)C(=O)CC(=O)C1=CC=CC=C1 VVXLFFIFNVKFBD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 2
- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 description 10
- 239000004830 Super Glue Substances 0.000 description 7
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 240000007182 Ochroma pyramidale Species 0.000 description 3
- -1 aromatic sulfonic acids Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011120 plywood Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Description
本発明は接着速度の速かなα−シアノアクリレ
ート系接着剤組成物に関し、詳細にはα−シアノ
アクリレートとジケトンとを含む接着剤組成物に
関する。
α−シアノアクリレート系接着剤は、被接着材
料の表面に付着する微量の水分によつてアニオン
重合が開始され、数秒で強固に硬化接着する瞬間
接着剤であり、光学、弱電、航空機、医学用等の
分野で広く用いられている。しかし、本質材料や
クロメート処理表面または酸性を呈する金属の酸
化表面等においては、α−シアノアクリレートの
アニオン重合性が抑制され、そのため接着剤塗布
から所望の接着力を示すまでに要する時間、すな
わち、硬化時間または接着速度が遅くなる傾向を
有する。特に木質材料の場合は、その樹液がpH4
〜６の酸性であるために硬化時間が長くなるだけ
でなく、その材質が多孔質であるのでα−シアノ
アクリレートが木質内部に浸透してしまい、その
ため接着が困難である。このような欠点を改良す
るため、従来プライマーとしてα−シアノアクリ
レート単量体のアニオン重を促進させる硬化剤を
被接着材料の一方に塗布処理する方法がとられて
来たが、二液型であるため、塗布回数が２回とな
る作業上の欠点やα−シアノアクリレート系接着
剤と分離保管せねばならない貯蔵上の問題、さら
には接着力がバラつき低下する等の問題が新たに
生じた。酸性表面に対して前記接着剤の硬化時間
を速くするためのその他の解決法として、例え
ば、前記接着剤に添加するアニオン重合防止剤の
量を通常よりも少なくする方法、およびα−シア
ノアクリレートの純度を高める方法が提案され
た。これらの方法も次のような理由から実用上問
題がある。すなわち、重合防止剤の量を抑えたα
−シアノアクリレート系接着剤または純度を高め
たものは、保存容器中に含まれる水分、または保
存中に容器に浸透する水分等により容器中でアニ
オン重合が序々に進行し、その結果、粘度の上昇
またはゲル化を生起し、長期保存に耐えることが
不可能であつた。
本発明者等は、従来のα−シアノアクリレート
系接着剤組成物にジケトンを加えることにより、
上記のような欠点をすべて解決できることを見い
出し、本発明を完成させるに至つた。
本発明の目的は、木質材料、クロメート処理表
面または酸性を呈する金属の酸化表面に対して速
い接着時間を示すα−シアノアクリレート系接着
剤組成物を提供することにある。本発明のその他
の目的は、長期保存性を有するα−シアノアクリ
レート接着剤組成物を提供することにある。
本発明によれば、これらの目的およびその他の
目的は、α−シアノアクリレートとジケトンとを
含んでなる接着速度の速やかな接着剤組成物によ
つて達成される。
以下、本発明を詳述する。
本発明の組成物に用い得るα−シアノアクリレ
ートは一般式
The present invention relates to an α-cyanoacrylate adhesive composition having a high adhesion speed, and more particularly to an adhesive composition containing α-cyanoacrylate and a diketone. α-Cyanoacrylate adhesive is an instant adhesive in which anionic polymerization is initiated by a small amount of moisture adhering to the surface of the adhered material, and it hardens and bonds in a few seconds.It is used in optical, light electrical, aircraft, and medical applications. It is widely used in fields such as However, on essential materials, chromate-treated surfaces, oxidized surfaces of acidic metals, etc., the anionic polymerization of α-cyanoacrylate is suppressed, and as a result, the time required from adhesive application to exhibiting the desired adhesive strength, i.e. Tends to slow curing time or adhesion speed. Especially in the case of wood materials, the sap of the wood has a pH of 4.
Not only does the curing time become longer due to the acidity of ~6, but also the porous nature of the material allows α-cyanoacrylate to penetrate into the interior of the wood, making it difficult to bond. In order to improve these drawbacks, conventional methods have been used in which a curing agent that accelerates the anionic weight of α-cyanoacrylate monomer is applied to one side of the bonded material as a primer, but a two-component type As a result, new problems have arisen, such as operational disadvantages in which the adhesive has to be applied twice, storage problems in that it must be stored separately from the α-cyanoacrylate adhesive, and further problems such as variations in adhesive strength and reduced adhesive strength. Other solutions to speed up the curing time of the adhesive for acidic surfaces include, for example, adding less anionic polymerization inhibitor to the adhesive than usual, and adding α-cyanoacrylate to the adhesive. A method to increase purity was proposed. These methods also have practical problems for the following reasons. In other words, α with a reduced amount of polymerization inhibitor
- For cyanoacrylate adhesives or those with increased purity, anionic polymerization gradually progresses in the storage container due to moisture contained in the storage container or moisture that permeates into the container during storage, resulting in an increase in viscosity. Otherwise, gelation occurred and it was impossible to withstand long-term storage. The present inventors have discovered that by adding a diketone to a conventional α-cyanoacrylate adhesive composition,
We have discovered that all of the above-mentioned drawbacks can be solved, and have completed the present invention. It is an object of the present invention to provide an alpha-cyanoacrylate adhesive composition that exhibits a fast adhesion time to wood materials, chromated surfaces or oxidized surfaces of acidic metals. Another object of the present invention is to provide an α-cyanoacrylate adhesive composition that has long shelf life. According to the present invention, these and other objects are achieved by a fast bonding adhesive composition comprising an alpha-cyanoacrylate and a diketone. The present invention will be explained in detail below. The α-cyanoacrylate that can be used in the composition of the present invention has the general formula
【式】で表わされる化
合物である。式中、Ｒはアルキル、アルケニル、
シクロヘキシル等であり、具体的にはメチル、エ
チル、ｎ−プロピル、イソプロピル、ｎ−ブチ
ル、イソブチル、ペンチル、ヘキシル、アリル、
プロパギル、シクロヘキシル、ベンジル、２−ク
ロロエチル、トリフルオロエチル等が挙げられ
る。これらの化合物は１種または２種以上の組合
せで用いることができる。また、本発明組成物に
用いられるジケトンは１、３−ジケトン（β−ジ
ケトン）、１、４−ジケトン（γ−ジケトン）等
であり、具体的には１、３−ジケトンとしてアセ
チルアセトン、ベンゾイルアセトン、ベンゾイル
トリフルオロアセトン、テノイルフルオロアセト
ン、トリフルオロアセチルアセトン、ヘキサフル
オロアセチルアセトン、２−フロイルトリフルオ
ロアセトン、ジベンゾイルメタン等があげられ、
１、４−ジケトンとしてアセトニルアセトン、フ
エナンシルアセトン等があげられる。ジケトンの
本発明組成物における含有量はα−シアノアクリ
レートの重量に対して0.1〜10重量％であり、好
ましくは0.1〜５重量％である。ジケトンの量が
0.1重量％以下では十分速い接着速度を得ること
が困難となり、一方10重量％を超えると保存安定
性が劣り、接着力が低下する。
本発明の組成物には、上記の２成分に加えて、
必要に応じて次のようなその他の成分を加えるこ
とができる。
() アニオン重合防止剤
二酸化硫黄、二酸化炭素、芳香族スルホン
酸、脂肪族スルホン酸、その他の有機酸等。
() ラジカル重合防止剤
ヒドロキノン、ヒドロキノンモノメチルエー
テル等。
() 増粘剤
ポリメチルメタクリレート、ポリ（α−シア
ノアクリレート）、アクリルゴム、セルロース
誘導体等。
() その他
香料、染料、顔料、可塑剤、熱安定剤。
これらのその他の成分は公知の所望量を本発明
の組成物に加えることができる。
上述したように、本発明の接着剤組成物は、木
質材料、クロメート処理表面および酸性を呈する
金属の酸化表面に対して数秒台の優れた瞬間接着
性を有し、しかも従来のものと同程度あるいはよ
り優れた保存性および剪断接着力を有するもので
あり、従つて実用上極めて有用な発明である。
以下、実施例により本発明をさらに詳述する。
例 １
α−シアノアクリレート100部に対し、第１表
に示す各種のジケトン0.5〜１重量％、ヒドロキ
ノン0.05重量％、二酸化硫黄50ppm、ポリメチル
メタクリレート３重量％を添加混合し、本発明の
組成物を製造した。また対照として、ジケトンの
みを除く他の上記各成分を含む組成物も製造し
た。これらの各種の組成物試料について下記の試
験を行なつた。
接着速度
25×100×５mmの〓ベニヤ材およびバルサ材試
験片を用意し、上記のようにして得られた各種試
料１滴を１試験片につき１試料ずつ塗布し、セツ
トタイムを調べることによつて接着速度を測定し
た。
剪断接着力
接着速度試験に用いた試験片を〓ベニヤ材およ
びバルサ材同志でそれぞれ対を作り、各対の一方
の面にそれぞれ試料１滴を塗布して貼合せ、室温
で５分間放置して硬化させた後テンシロン引張試
験機を使用して、〓ベニヤ材に対しては60Kg／
cm2、バルサ材に対しては12Kg／cm2の荷重を加え、
各試験片の変化を観察した。
貯蔵安定性
各試料をそれぞれ50c.c.ずつ100c.c.の保存容器に
入れ、密封して温度70℃の恒温室内に貯蔵し、５
日経過後の各試料のゲル化の有無等を調べること
によつて貯蔵安定性を評価した。
これらの３種の試験によつて得られた結果を第
１表に示す。It is a compound represented by the formula: In the formula, R is alkyl, alkenyl,
cyclohexyl, etc., specifically methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, pentyl, hexyl, allyl,
Examples include propargyl, cyclohexyl, benzyl, 2-chloroethyl, trifluoroethyl, and the like. These compounds can be used alone or in combination of two or more. Further, diketones used in the composition of the present invention include 1,3-diketones (β-diketones), 1,4-diketones (γ-diketones), etc. Specifically, the 1,3-diketones include acetylacetone and benzoylacetone. , benzoyltrifluoroacetone, thenoylfluoroacetone, trifluoroacetylacetone, hexafluoroacetylacetone, 2-furoyltrifluoroacetone, dibenzoylmethane, etc.
Examples of the 1,4-diketone include acetonylacetone and phenancylacetone. The content of diketone in the composition of the present invention is 0.1 to 10% by weight, preferably 0.1 to 5% by weight, based on the weight of α-cyanoacrylate. The amount of diketone
If it is less than 0.1% by weight, it will be difficult to obtain a sufficiently fast adhesion speed, while if it exceeds 10% by weight, storage stability will be poor and adhesive strength will decrease. In addition to the above two components, the composition of the present invention includes:
Other ingredients such as the following can be added as necessary. () Anionic polymerization inhibitors Sulfur dioxide, carbon dioxide, aromatic sulfonic acids, aliphatic sulfonic acids, other organic acids, etc. () Radical polymerization inhibitors Hydroquinone, hydroquinone monomethyl ether, etc. () Thickeners Polymethyl methacrylate, poly(α-cyanoacrylate), acrylic rubber, cellulose derivatives, etc. () Others Fragrances, dyes, pigments, plasticizers, heat stabilizers. These other components can be added to the composition of the present invention in known desired amounts. As mentioned above, the adhesive composition of the present invention has excellent instantaneous adhesion to wood materials, chromate-treated surfaces, and oxidized surfaces of acidic metals in the order of several seconds, and is comparable to conventional adhesives. Alternatively, it has better storage stability and shear adhesive strength, and is therefore an extremely useful invention in practice. Hereinafter, the present invention will be explained in further detail with reference to Examples. Example 1 To 100 parts of α-cyanoacrylate, 0.5 to 1% by weight of various diketones shown in Table 1, 0.05% by weight of hydroquinone, 50ppm of sulfur dioxide, and 3% by weight of polymethyl methacrylate were added and mixed to form a composition of the present invention. was manufactured. As a control, a composition containing each of the above-mentioned components except for the diketone was also produced. The following tests were conducted on these various composition samples. Adhesion speed Prepare plywood and balsa wood test pieces of 25 x 100 x 5 mm, apply one drop of each sample obtained as above to each test piece, and check the set time. The adhesion speed was measured. Shear Adhesion Strength The test pieces used for the adhesion speed test were made into pairs of plywood and balsa wood, one drop of the sample was applied to one side of each pair, the pieces were pasted together, and left at room temperature for 5 minutes. After curing, use a Tensilon tensile tester to test the veneer material at 60 kg/
cm 2 , and for balsa wood, apply a load of 12Kg/cm 2 ,
Changes in each test piece were observed. Storage Stability Place 50 c.c. of each sample in a 100 c.c. storage container, seal and store in a thermostatic chamber at a temperature of 70°C.
Storage stability was evaluated by examining the presence or absence of gelation of each sample after a day had passed. The results obtained from these three tests are shown in Table 1.
【表】
第１表の結果から明らかなように、ジケトンを
含む本発明の組成物は木質材料表面に対して２〜
10秒で接着するという十分速い接着速度を有し、
しかも剪断接着力および貯蔵安定性にも富んでい
た。一方、ジケトンを含まない組成物は接着速度
が大巾に遅く、貯蔵安定性も劣つていた。
例 ２
被接着材料として第２表の各種木材、金属、そ
の他を選び、例1.の試料２および試料６（対照）
を用いてセツトタイムを測定た。測定方法は例1.
の接着時間の試験と同様にして行なつた。得られ
た結果を第２表に示す。[Table] As is clear from the results in Table 1, the composition of the present invention containing a diketone has a
It has a sufficiently fast adhesion speed that adheres in 10 seconds,
Furthermore, it had excellent shear adhesive strength and storage stability. On the other hand, compositions containing no diketone had significantly slower adhesion speeds and poor storage stability. Example 2 Select various woods, metals, and others listed in Table 2 as the materials to be bonded, and sample 2 and sample 6 (control) from Example 1.
The set time was measured using The measurement method is Example 1.
The test was carried out in the same manner as the adhesion time test. The results obtained are shown in Table 2.
【表】【table】
【表】
第２表の結果から、本発明の組成物は試験した
すべての被接着材料についてジケトンを加えない
ものよりも著しく速い接着性を示すことが判明し
た。
例 ３
ジケトンとしてアセチルアセトンを用い、その
添加量を変化させる以外は例１と同様にして接着
剤組成物を製造し、例１の試験をくり返した。得
られた結果を第３表に示す。Table 2 The results in Table 2 show that the compositions of the present invention exhibit significantly faster adhesion than those without added diketones on all bonded materials tested. Example 3 An adhesive composition was produced in the same manner as in Example 1 except that acetylacetone was used as the diketone and the amount added was varied, and the test in Example 1 was repeated. The results obtained are shown in Table 3.
【表】
第３表の結果から明らかなように、ジケトンの
添加量は0.1重量％以下になると十分な接着速度
が得にくくなり、一方、10重量％を超えると貯蔵
安定性および剪断接着力に問題を生じる。従つ
て、本発明の組成物における化合物（）の添加
量は0.1〜10重量％の範囲であることが実用上好
ましい。[Table] As is clear from the results in Table 3, if the amount of diketone added is less than 0.1% by weight, it will be difficult to obtain a sufficient adhesion speed, while if it exceeds 10% by weight, storage stability and shear adhesive strength will be affected. cause problems. Therefore, it is practically preferable that the amount of compound () added in the composition of the present invention is in the range of 0.1 to 10% by weight.
Claims (1)
ヘキシルである）で表わされるα−シアノアクリ
レートと、１、３ジケトンおよび１、４ジケトン
の群から選択されるジケトンとからなるα−シア
ノアクリレート系接着剤組成物。 ２ 特許請求の範囲第１項に記載の組成物におい
て、１、３ジケトンがアセチルアセトン、ベンゾ
イルアセトン、ベンゾイルトリフルオロアセト
ン、テノイルフルオロアセトン、トリフルオロア
セチルアセトン、ヘキサフルオロアセチルアセト
ン、２−フロイルトリフルオロアセトンおよびジ
ベンゾイルメタンの群から選択されるものである
組成物。 ３ 特許請求の範囲第１項に記載の接着剤組成物
において、１、４ジケトンがアセトニルアセトン
およびフエナンシルアセトンの群から選択される
ものである組成物。 ４ 特許請求の範囲第１項に記載の接着剤組成物
において、α−シアノアクリレートに対するジケ
トン量は重量で0.1〜10重量％である組成物。[Claims] 1. General formula (wherein R is alkyl, alkenyl or cyclohexyl) and a diketone selected from the group of 1,3 diketones and 1,4 diketones. thing. 2. In the composition according to claim 1, the 1,3 diketone is acetylacetone, benzoylacetone, benzoyltrifluoroacetone, thenoylfluoroacetone, trifluoroacetylacetone, hexafluoroacetylacetone, 2-furoyltrifluoroacetone, and A composition selected from the group of dibenzoylmethane. 3. An adhesive composition according to claim 1, wherein the 1,4 diketone is selected from the group of acetonylacetone and phenancylacetone. 4. The adhesive composition according to claim 1, wherein the amount of diketone relative to α-cyanoacrylate is 0.1 to 10% by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14738280A JPS5770170A (en) | 1980-10-21 | 1980-10-21 | Adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14738280A JPS5770170A (en) | 1980-10-21 | 1980-10-21 | Adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5770170A JPS5770170A (en) | 1982-04-30 |
| JPH0147504B2 true JPH0147504B2 (en) | 1989-10-13 |
Family
ID=15428978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14738280A Granted JPS5770170A (en) | 1980-10-21 | 1980-10-21 | Adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5770170A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57109876A (en) * | 1980-12-27 | 1982-07-08 | Matsumoto Seiyaku Kogyo Kk | Adhesive composition |
| US5039753A (en) * | 1987-10-22 | 1991-08-13 | Loctite (Ireland) Ltd | Polymers comprising betadiketone groups and polymerizable compositions containing said polymers |
-
1980
- 1980-10-21 JP JP14738280A patent/JPS5770170A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5770170A (en) | 1982-04-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4170585A (en) | Adhesive composition | |
| CA2356749C (en) | Activator for cyanacrylate adhesives | |
| US4042442A (en) | 2-Cyanoacrylate adhesive composition | |
| US6835789B1 (en) | Cyanoacrylate compositions | |
| US6995227B2 (en) | Activator compositions for cyanoacrylate adhesives | |
| EP1807476B1 (en) | Shock resistant cyanoacrylate compositions | |
| US6475331B1 (en) | Cyanoacrylate compositions | |
| US4569976A (en) | Redox cure system for acrylic adhesive compositions | |
| US4430480A (en) | Two-part composition with activator enriched with dihydropyridine ingredients | |
| JPH0340751B2 (en) | ||
| JP2886426B2 (en) | Cyanoacrylate adhesive composition and method for imparting thermal stability thereof | |
| EP0105062A1 (en) | Coloured cyanoacrylate adhesive composition | |
| CZ20011972A3 (en) | Substance for bonding, coating and sealing, containing cyanoacrylates and aldehyde or ketone condensation products | |
| JPH0147504B2 (en) | ||
| KR0133659B1 (en) | Adhesive composition | |
| JPH0141668B2 (en) | ||
| JPH0150268B2 (en) | ||
| US3948794A (en) | Adhesive compositions containing a cyanoacrylate and itaconic anhydride | |
| GB2069512A (en) | Cyanoacrylate Adhesive Compositions | |
| EP0239890A2 (en) | Opaque cyanoacrylate adhesives and coatings | |
| SU668332A1 (en) | Adhesive composition | |
| JPH0362747B2 (en) | ||
| SU138301A1 (en) | Cold Curing Adhesive | |
| JP2022525641A (en) | Two-component curable composition | |
| BE828512Q (en) | ADHESIVE PRODUCTS BASED ON VINYL MONOMERS |