JPS5966473A - Thickening of alpha-cyanoacrylate adhesive - Google Patents
Thickening of alpha-cyanoacrylate adhesiveInfo
- Publication number
- JPS5966473A JPS5966473A JP17668082A JP17668082A JPS5966473A JP S5966473 A JPS5966473 A JP S5966473A JP 17668082 A JP17668082 A JP 17668082A JP 17668082 A JP17668082 A JP 17668082A JP S5966473 A JPS5966473 A JP S5966473A
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- methacrylate
- copolymer
- polymethyl methacrylate
- cyanoacrylate
- 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 14
- 239000004830 Super Glue Substances 0.000 title claims abstract description 10
- 230000008719 thickening Effects 0.000 title abstract description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims abstract description 21
- 239000004926 polymethyl methacrylate Substances 0.000 claims abstract description 21
- 229920001577 copolymer Polymers 0.000 claims abstract description 12
- 150000002148 esters Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 abstract description 19
- 230000001070 adhesive effect Effects 0.000 abstract description 19
- 229920000058 polyacrylate Polymers 0.000 abstract description 15
- -1 tetrahydrofurfuryl Chemical group 0.000 abstract description 8
- 229920000642 polymer Polymers 0.000 abstract description 7
- 239000002562 thickening agent Substances 0.000 abstract description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 abstract 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 229920001651 Cyanoacrylate Polymers 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920002689 polyvinyl acetate Polymers 0.000 description 3
- 239000011118 polyvinyl acetate Substances 0.000 description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 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
- 230000001771 impaired effect Effects 0.000 description 1
- DOULWWSSZVEPIN-UHFFFAOYSA-N isoproturon-monodemethyl Chemical compound CNC(=O)NC1=CC=C(C(C)C)C=C1 DOULWWSSZVEPIN-UHFFFAOYSA-N 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000000463 material Substances 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
- LKEDKQWWISEKSW-UHFFFAOYSA-N nonyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCOC(=O)C(C)=C LKEDKQWWISEKSW-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000120 polyethyl acrylate Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、Ｑ！−シアノアクリレート系接着剤を増粘す
る方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides Q! - A method of thickening a cyanoacrylate adhesive.
更に詳しくは、α−シアノアクリレートに重量平均分子
量２０万以上のポリメタクリル酸メチルとそれ以外のポ
リメタクリル酸エステル捷だけ、ポリアクリル酸エステ
ルの共重合体を配合してなるα−シアノアクリレート系
接着剤組成物に関する。More specifically, α-cyanoacrylate adhesive is made by blending α-cyanoacrylate with a copolymer of polymethyl methacrylate having a weight average molecular weight of 200,000 or more, other polymethacrylic esters, and polyacrylic ester. The present invention relates to a drug composition.
本発明の対象になる接着剤の主成分は次の一般式をもつ
化合物である。The main component of the adhesive that is the object of the present invention is a compound having the following general formula.
（−Ｌ式において、ＲはＣ３〜Ｃ６のアルキル基、アリ
ル基、アルコキシアルキル基、テトラヒドロフルフリル
基、フェニル基、シクロヘキシル基ヲアラわす。）
この種の化合物は、常温で流動性の良い無色透明の液体
であるが、これを物体の表面に薄膜状に塗布し、大気中
に数時間暴露すれば液膜は急速に硬化し強固々固体皮膜
を形成する。(In the -L formula, R represents a C3 to C6 alkyl group, allyl group, alkoxyalkyl group, tetrahydrofurfuryl group, phenyl group, or cyclohexyl group.) This type of compound is colorless and transparent with good fluidity at room temperature. If this liquid is applied as a thin film to the surface of an object and exposed to the atmosphere for several hours, the liquid film will rapidly harden and form a strong solid film.
この性質を二物体間の接着に応用し、接着剤を被着体の
表面に塗布し、単に接着面を重ね合わせる事により、何
等の加圧加温等を要せずに数秒ないし数十秒の間にきわ
めて強固に接着する。α−シアノアクリレートはこの様
な性質を有するため、これを主成分とする接着剤は一般
に瞬間接着剤と呼ばれている。Applying this property to bonding between two objects, by applying the adhesive to the surface of the adherend and simply overlapping the adhesive surfaces, it can be applied for several seconds to tens of seconds without any pressure or heating. The bond between the two is very strong. Since α-cyanoacrylate has such properties, adhesives containing it as a main component are generally called instant adhesives.
α−シアノアクリレートを主成分とする瞬間接着剤は、
精密機器類、木工家具類、弱電関係機器類等の分野で幅
広く使用され、一般家庭用としても需要を伸ばしている
。Instant adhesives whose main component is α-cyanoacrylate are
It is widely used in fields such as precision instruments, wooden furniture, and light electrical equipment, and demand is also growing for general household use.
Ｉ７か１２、これらの…冷の中で、未香ＪｆＩ 価鳩
材料の様な多孔質面には、低粘度品を使用すると浸透が
激しく、接着層が１゛分形成されず接着力が発現さねな
い。寸だ、平滑面であっても低粘度のα−シアノアクリ
レート系接着剤を用いると、接着部以外への流出を起こ
し、接着部以外の美観が著しくそこなわれる事がある。I7 or 12, these... In cold conditions, if a low viscosity product is used on a porous surface such as unscented JfI material, it will penetrate violently and an adhesive layer will not be formed for 1 minute and adhesive strength will not be developed. I don't know. Even on a smooth surface, if a low-viscosity α-cyanoacrylate adhesive is used, it may leak out to areas other than the bonded area, and the aesthetics of areas other than the bonded area may be significantly impaired.
そこで、これらの問題を解決するために、接着剤自体を
増粘する方法がとられている。しかし、α−シアノアク
リレートは非常に高いアニオン重合性を有しているだめ
、α−シアノアクリレートに溶解するものであっても経
時後増粘されゲル化捷たは固化を起こすものがある。こ
れは、増粘剤として用いる高分子の基質に起因するだけ
て々く、それに含有される触媒、水分、捷だは他のアル
カリ成分などが貯蔵安定性に悪影響を及ぼすためである
。Therefore, in order to solve these problems, methods have been taken to increase the viscosity of the adhesive itself. However, α-cyanoacrylate has extremely high anionic polymerizability, so even those that dissolve in α-cyanoacrylate may thicken over time and cause gelation, shrinkage, or solidification. This is not only due to the polymeric substrate used as the thickener, but also because the catalyst, moisture, sulfate or other alkaline components contained therein have an adverse effect on storage stability.
これ捷てに、α−シアノアクリレート系接着剤の増粘剤
として名種高分子が検討された。たとえば、ポリ酢酸セ
ルロース、ポリ酢酸ビニル、ポリメタクリル酸メチルな
どである。この中で、ポリ酢酸セルロースはアルカリ性
成分を含有１７ており実用化するためには酸洗浄を要す
る。しかし、酸洗浄を行って聞合してもヤツトタイムが
延長する等、性能に悪影響を及ぼす事がある。ポリ酢酸
ビニルは、軟化点が低く水分を除去するにも３５°Ｃ以
−，ｈで乾燥できないだめ、真空乾燥の装置を必要とす
る。ポリツククリル酸メチルが通常よく使用されるが、
所定の粘度に達するためには多］辻のポリマーを配合し
なければならない。このことは前述のポリ酢酸ビニル、
ポリ酢酸セルロースについても同様の事が言える。捷た
、特にポリメタクリル酸メチルについてはポリマー自体
が硬いので、α−シアノアクリレートの欠点の−っであ
る硬さをより犬にし接着強度を低下させる原因ともなる
だめ好ましくない。In response to this, various high-quality polymers were investigated as thickeners for α-cyanoacrylate adhesives. Examples include polycellulose acetate, polyvinyl acetate, and polymethyl methacrylate. Among these, polycellulose acetate contains an alkaline component17 and requires acid washing for practical use. However, even if acid cleaning is performed, performance may be adversely affected, such as prolonging cleaning time. Polyvinyl acetate has a low softening point and cannot be dried at temperatures above 35°C for hours to remove moisture, so it requires a vacuum drying device. Polymethyl succinate is commonly used, but
In order to reach the desired viscosity, multiple polymers must be blended. This means that the aforementioned polyvinyl acetate,
The same can be said of polycellulose acetate. Curved polymethyl methacrylate, in particular, is undesirable because the polymer itself is hard, which increases the hardness, which is a disadvantage of α-cyanoacrylate, and causes a decrease in adhesive strength.
そこで、本発明者らは鋭意増粘剤の検討を１〜だ結果、
重量平均分子量２０万以上のポリツククリル酸メチルと
それ以外のポリメタクリル酸エステル捷たは、アクリル
酸エステルの共重合体がα−シアノアクリレート系接着
剤の増粘剤として好適であることを見い出した。Therefore, the present inventors conducted a thorough study on thickeners and found that
It has been found that a copolymer of polymethyl methacrylate having a weight average molecular weight of 200,000 or more and other polymethacrylic esters or acrylic esters is suitable as a thickener for α-cyanoacrylate adhesives.
本発明に使用される１隈平均分子量２０万以−１−の共
重合体中のポリメタクリル酸メチル以外のポリメタクリ
ル酸エステルまだはポリアクリル酸エステルとしては例
えば、ポリツククリル酸メチル、ボリメククリル酸−ｎ
−プロピル、ポリメタクリル酸−１ｓＯ−プロピル、ポ
リメタクリル酸−ｎ−ブチル、ポリメタクリル酸−１ｓ
ｏ−ブチル、ポリメタクリル酸−ｎ−ヘキシル、ポリメ
タクリル酸−ｎ−ヘプチル、ポリメタクル酸−〇−オク
チル、ポリメタクリル酸−２−エチルヘキシル、ポリメ
タクリル酸ノニル、ポリメタクリル酸メトキシエチル、
ポリメタクリル酸メ１〜ギシプロピル、ポリメタクリル
酸メトキシエチル、ポリメタクリル酸エトキシプロピル
、ポリメタクリル酸アリル、ポリメタクリル酸テトラヒ
ドロフルフリル、ポリアクリル酸メチル、ポリアクリル
酸エチル、ポリアクリル酸−ｎ−プロピル、ポリアクリ
ル酸−１ｓｏ−プロピル、ポリアクリル酸−ｎ−ブチル
、ポリアクリル酸−１ｓｏ−ブチル、ポリアクリル酸−
〇−ヘキシル、ポリアクリル酸−〇−ヘプチル、ポリア
クリル酸−ｎ−オタチル、ポリアクリル酸−２−エチル
ヘキシル、ポリアクリル酸ノニル、ポリアクリル酸メト
キシエチル、ポリアクリル酸メトキシプロピル、ポリア
クリル酸エトキシエチル、ポリアクリル酸エトキシプロ
ピル、ポリアクリル酸アリル、ポリアクリル酸テトラヒ
ドロフルフリルなどが挙げられ、これらのエステルは単
独捷たけ２種以−Ｌ混用されたものでもよい。捷だこれ
らのエステルは共重合体中に１〜５０モル％、好捷しく
は２〜３５モル％存在するのが望ましい。１モル％以下
では以下に述べる本発明効果が認められず、３５モル％
を超えるに従って次第にポリツククリル酸メチル、特に
重量平均分子量ｌＯ万以上のポリメタクリル酸メチルの
性質に近着き、５０モル％を超えると共重合体としての
本発明の特性を失う。Examples of polymethacrylic esters other than polymethyl methacrylate in the copolymer having an area average molecular weight of 200,000 or more used in the present invention include polymethyl methacrylate, polymethacrylic acid-n
-Propyl, polymethacrylic acid-1sO-propyl, polymethacrylic acid-n-butyl, polymethacrylic acid-1s
o-butyl, poly-n-hexyl methacrylate, poly-n-heptyl methacrylate, poly-octyl methacrylate, poly-2-ethylhexyl methacrylate, poly-nonyl methacrylate, polymethoxyethyl methacrylate,
polymethacrylate-gicipropyl, polymethoxyethyl methacrylate, polyethoxypropyl methacrylate, polyallyl methacrylate, polytetrahydrofurfuryl methacrylate, polymethyl acrylate, polyethyl acrylate, polyn-propyl acrylate, 1so-propyl polyacrylate, n-butyl polyacrylate, 1so-butyl polyacrylate, polyacrylate
〇-hexyl, 〇-heptyl polyacrylate, n-otatyl polyacrylate, 2-ethylhexyl polyacrylate, nonyl polyacrylate, methoxyethyl polyacrylate, methoxypropyl polyacrylate, ethoxyethyl polyacrylate , ethoxypropyl polyacrylate, allyl polyacrylate, tetrahydrofurfuryl polyacrylate, etc. These esters may be used alone or in a mixture of two or more. These esters are preferably present in the copolymer in an amount of 1 to 50 mol%, preferably 2 to 35 mol%. At 1 mol% or less, the effects of the present invention described below are not observed, and at 35 mol%
As the amount exceeds 50 mol %, the properties gradually approach that of polymethyl methacrylate, especially polymethyl methacrylate having a weight average molecular weight of 10,000 or more, and when it exceeds 50 mol %, the properties of the present invention as a copolymer are lost.
本発明の方法によれば重量平均分子量２０乃以りのポリ
メタクリル酸メチルとその他の（メタ）７ ’） Ｉｆ
ル酸毛フ−’； Ｉｌ、Ｌ小妊幣ム汁せ−ハ１ ・−
・−クリレートに小品添加するだけで相当の増粘りｂ果
を示す。従って同じ粘度の接着剤を得るに当って従前の
ポリメタクリル酸メチル、特に重量平均分子ｌｅｔ １
０万以下のポリメタクリル酸メチルを大ｎ１に添加する
ために生ずるセットタイムの遅れや、接着強さの低下々
どの欠点が改善されるようになった。According to the method of the present invention, polymethyl methacrylate having a weight average molecular weight of 20 or more and other (meth)7') If
Il, L small pregnancy juice seha 1 ・-
・--Significant thickening can be achieved by simply adding a small amount to acrylate. Therefore, in order to obtain an adhesive with the same viscosity, the conventional polymethyl methacrylate, especially the weight average molecular weight let 1
The disadvantages such as delay in set time and decrease in adhesive strength caused by adding polymethyl methacrylate of 0,000 or less to large n1 have been improved.
本発明のＱノーシアノアクリレート系接着剤に“、α−
シアノアクリレートに適宜のポリメタクリル酸メチルと
それ以外のポリメタクリル酸エステルの共重合体を混合
攪拌するだけで容易に製造する４■が出来る。In the Q-free cyanoacrylate adhesive of the present invention, α-
4) can be easily produced by simply mixing and stirring a suitable copolymer of polymethyl methacrylate and other polymethacrylate ester with cyanoacrylate.
捷だ、本発明の接着剤には従来からのα−シアノアクリ
レート系接着剤に添加して…いられる安定剤、可塑剤、
着色剤、強度向−に剤、界面活性剤、溶剤等も添加使用
する事が出来る。The adhesive of the present invention contains stabilizers, plasticizers, etc. that can be added to conventional α-cyanoacrylate adhesives.
Colorants, strength agents, surfactants, solvents, etc. can also be added.
以下に実施例を挙げて本発明を具体的に説明する。The present invention will be specifically described below with reference to Examples.
実施例１．〜３．比較例１．〜４゜
亜硫酸ガス０００２重量％およびハイドロキノンＯ１重
置％を含有するエチル−〇−シアノアクリレートに表１
に示す各種ポリマーを添加して接着剤組成物を調製した
。これらの接着剤の粘度をＢＬ型粘度計で、各ローター
回転数を３０に１７、接着剤の液温を２０°Ｃに調節し
測定した。Example 1. ~3. Comparative example 1. ~4゜ Ethyl-〇-cyanoacrylate containing 0002% by weight of sulfur dioxide gas and 1% by weight of hydroquinone O in Table 1
Adhesive compositions were prepared by adding the various polymers shown below. The viscosity of these adhesives was measured using a BL type viscometer with the rotor rotation speed adjusted to 30 to 17 and the adhesive liquid temperature adjusted to 20°C.
＼
表１より判る様に、重量平均分子量２０万以−１−のポ
リメタクリル酸メチルとポリメタクリル酸メチル以外の
ポリメタクリル酸エステル、捷たはポリアクリル酸エス
テルの共重合体は、重量平均分子量の低いポリメタクリ
ル酸メチルやポリメタクリル酸メチルとポリメタクリル
酸メチル以外のポリメタクリル酸エステルの重合体、賛
だけポリメタクリル酸メチルとポリアクリル酸エステル
との共重合体よりも、増粘効果が非常に良い事が判る。＼ As can be seen from Table 1, copolymers of polymethyl methacrylate with a weight average molecular weight of 200,000 or more -1- and polymethacrylic esters other than polymethyl methacrylate, kneaded or polyacrylic esters have a weight average molecular weight of 200,000 or more. Polymethyl methacrylate, a polymer of polymethyl methacrylate and a polymethacrylic ester other than polymethyl methacrylate, and a copolymer of polymethyl methacrylate and polyacrylic ester have a much thickening effect. It turns out to be good.
実施例４〜６． 比較例５．〜８゜
亜硫酸ガス０００２重量％およびノ・イドロキノン０１
重量％を含有するエチル−〇−シアノアクリレートに表
２に示す各種ポリマーを略同−粘度になる様に添加し、
各接着剤組成物のセットタイム、および引張剪断強度を
ＪＩＳＫ６８６１に準じて試験した。保存安定性は容量
２０ＣＣの低密度ポリエチレン容器に、各接着剤組成物
を、２０ｙ入れ、７０°Ｃ１７日間暴露した後粘度測定
を行い、粘度変化により判定した。Examples 4-6. Comparative example 5. ~8゜Sulfur dioxide gas 0002% by weight and hydroquinone 01
Various polymers shown in Table 2 were added to ethyl-〇-cyanoacrylate containing approximately the same viscosity in weight%,
The set time and tensile shear strength of each adhesive composition were tested according to JIS K6861. Storage stability was determined by placing each adhesive composition for 20 y in a 20 cc low-density polyethylene container, exposing it to 70° C. for 17 days, then measuring the viscosity, and determining the change in viscosity.
Claims (1)
それ以外のポリメタクリル酸エステルまたは、」ニリア
クリル酸エステルの共重合体を配合１−てなるα−シア
ノアクリレート系接着剤組成物。An α-cyanoacrylate adhesive composition comprising a copolymer of polymethyl methacrylate having a weight average molecular weight of 200,000 or more and other polymethacrylic esters or nilyacrylic esters.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17668082A JPS5966473A (en) | 1982-10-07 | 1982-10-07 | Thickening of alpha-cyanoacrylate adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17668082A JPS5966473A (en) | 1982-10-07 | 1982-10-07 | Thickening of alpha-cyanoacrylate adhesive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5966473A true JPS5966473A (en) | 1984-04-14 |
| JPH0415267B2 JPH0415267B2 (en) | 1992-03-17 |
Family
ID=16017839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17668082A Granted JPS5966473A (en) | 1982-10-07 | 1982-10-07 | Thickening of alpha-cyanoacrylate adhesive |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5966473A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6833196B1 (en) * | 2002-06-24 | 2004-12-21 | Henkel Corporation | Acrylic-toughened cyanoacrylate compositions |
| US9944830B2 (en) | 2005-07-11 | 2018-04-17 | Henkel IP & Holding GmbH | Toughened cyanoacrylate compositions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69503844T2 (en) | 1994-06-08 | 1999-04-22 | Taoka Chemical Co., Ltd., Osaka | Alphacyanoacrylate-based adhesive composition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52130831A (en) * | 1976-04-27 | 1977-11-02 | Taoka Chem Co Ltd | Adhesive |
| JPS54119536A (en) * | 1978-03-10 | 1979-09-17 | Taoka Chem Co Ltd | Adhesive |
-
1982
- 1982-10-07 JP JP17668082A patent/JPS5966473A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52130831A (en) * | 1976-04-27 | 1977-11-02 | Taoka Chem Co Ltd | Adhesive |
| JPS54119536A (en) * | 1978-03-10 | 1979-09-17 | Taoka Chem Co Ltd | Adhesive |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6833196B1 (en) * | 2002-06-24 | 2004-12-21 | Henkel Corporation | Acrylic-toughened cyanoacrylate compositions |
| US9944830B2 (en) | 2005-07-11 | 2018-04-17 | Henkel IP & Holding GmbH | Toughened cyanoacrylate compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0415267B2 (en) | 1992-03-17 |
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