JPH037786A - Adhesive composition - Google Patents
Adhesive compositionInfo
- Publication number
- JPH037786A JPH037786A JP6868090A JP6868090A JPH037786A JP H037786 A JPH037786 A JP H037786A JP 6868090 A JP6868090 A JP 6868090A JP 6868090 A JP6868090 A JP 6868090A JP H037786 A JPH037786 A JP H037786A
- Authority
- JP
- Japan
- Prior art keywords
- cyanoacrylate
- alpha
- adhesive composition
- acid
- pts
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 11
- 230000001070 adhesive effect Effects 0.000 title description 7
- 239000000853 adhesive Substances 0.000 title description 6
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical group OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims abstract description 18
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims abstract description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000004830 Super Glue Substances 0.000 claims description 7
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 abstract description 3
- JYTXVMYBYRTJTI-UHFFFAOYSA-N 2-methoxyethyl 2-cyanoprop-2-enoate Chemical compound COCCOC(=O)C(=C)C#N JYTXVMYBYRTJTI-UHFFFAOYSA-N 0.000 abstract description 2
- 229910004039 HBF4 Inorganic materials 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract description 2
- IPDQIHIYQHAUCO-UHFFFAOYSA-N phenyl 2-cyanoprop-2-enoate Chemical compound N#CC(=C)C(=O)OC1=CC=CC=C1 IPDQIHIYQHAUCO-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002023 wood Substances 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 230000000391 smoking effect Effects 0.000 abstract 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 6
- 238000010526 radical polymerization reaction Methods 0.000 description 5
- -1 2-ethoxyethyl Chemical group 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 229940079877 pyrogallol Drugs 0.000 description 3
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- 240000002234 Allium sativum Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 229920001651 Cyanoacrylate Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920000800 acrylic rubber Polymers 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 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 2
- 230000000052 comparative effect Effects 0.000 description 2
- 235000004611 garlic Nutrition 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004823 Reactive adhesive Substances 0.000 description 1
- QXNIBPDSSDVBQP-UHFFFAOYSA-N acetic acid;2-methylpropanoic acid Chemical compound CC(O)=O.CC(C)C(O)=O QXNIBPDSSDVBQP-UHFFFAOYSA-N 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VRKSJXIKRFNNFZ-UHFFFAOYSA-N benzyl 2-cyanoprop-2-enoate Chemical compound N#CC(=C)C(=O)OCC1=CC=CC=C1 VRKSJXIKRFNNFZ-UHFFFAOYSA-N 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- KWKVJEUILVQMRR-UHFFFAOYSA-N decyl 2-cyanoprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(=C)C#N KWKVJEUILVQMRR-UHFFFAOYSA-N 0.000 description 1
- LFJLAWZRNOKTDN-UHFFFAOYSA-N dodecyl 2-cyanoprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(=C)C#N LFJLAWZRNOKTDN-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- ZTYMNUBYYQNBFP-UHFFFAOYSA-N propyl 2-cyanoprop-2-enoate Chemical compound CCCOC(=O)C(=C)C#N ZTYMNUBYYQNBFP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- LEMQFBIYMVUIIG-UHFFFAOYSA-N trifluoroborane;hydrofluoride Chemical compound F.FB(F)F LEMQFBIYMVUIIG-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は貯蔵安定性の優れたα−シアノアクリレート系
接着剤組成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to an α-cyanoacrylate adhesive composition having excellent storage stability.
〈従来の技術〉
α−シアノアクリレート系接着剤はα−シアノアクリレ
ートモノマーを主成分とした反応型接着剤であるために
、貯蔵期間１１０こ接着剤容器内でα−シアノアクリレ
ートモノマーがラジカル重合又はアニオン重合して硬化
することがあるため、重合防止剤を安定剤として添加し
貯蔵安定化を図−）でいる。α−シアノアクリレートモ
ノマーのラジカル重合防止剤としては、ハイドロキノン
、ハイドロキノンモノメチルエーテル、カテコール、ピ
ロガロール、ビスフェノールＡなどが使用されており、
１〜５０００ｐｐｍの添加量で常温貯蔵時におけるラジ
カル重合の防止を図っている。<Prior art> Since α-cyanoacrylate adhesive is a reactive adhesive mainly composed of α-cyanoacrylate monomer, α-cyanoacrylate monomer undergoes radical polymerization or Since it may undergo anionic polymerization and harden, a polymerization inhibitor is added as a stabilizer to stabilize storage. Hydroquinone, hydroquinone monomethyl ether, catechol, pyrogallol, bisphenol A, etc. are used as radical polymerization inhibitors for α-cyanoacrylate monomers.
The addition amount of 1 to 5000 ppm is intended to prevent radical polymerization during storage at room temperature.
一方、アニオン重合は、水分、アミン、アンモニアなど
の塩基性物質が微量混入して開始されるもので、このア
ニオン重合による増粘、ゲル化を防止するもノドして、
ＳＯ，、ＳＯ３，５ｏｃｋ７、ＳＯ２Ｃ１□、ＨＦ、
ＢＦＪ、 Ｂ Ｆ、エーテルコンプレックス、Ｎｏ２、
パラトルエンスルホン酸、メタンスルホン酸、プロパン
サルトン、りん酸、硫酸などが公知である。On the other hand, anionic polymerization is initiated by the introduction of a trace amount of basic substances such as water, amines, and ammonia, and although thickening and gelation due to this anionic polymerization can be prevented,
SO,, SO3,5ock7, SO2C1□, HF,
BFJ, BF, Ether Complex, No2,
Paratoluenesulfonic acid, methanesulfonic acid, propanesultone, phosphoric acid, sulfuric acid, and the like are known.
〈発明が解決しようとする課題〉
しかしながら、これ１ン、のアニオン重合防止剤は添加
されることにより、セラ１へタイムが遅くなり瞬間接着
性がそこなわれたり、ガス状である為取扱いや濃度調整
が困難であったり、Ｓ０３やＢＦ３エーテルコンプレッ
クスの様に発煙し、着色しやすい等の欠点を有している
。従って、当業界ではこの様な問題のないより優れたア
ニオン重合防止剤が求められている。<Problems to be Solved by the Invention> However, the addition of this anionic polymerization inhibitor slows down the time to Cera 1, impairs instant adhesive properties, and makes it difficult to handle since it is in a gaseous state. It has drawbacks such as difficulty in adjusting the concentration, emitting smoke like S03 and BF3 ether complex, and being easily colored. Therefore, there is a need in the art for a better anionic polymerization inhibitor that does not have these problems.
〈課題を解決するための手段〉
本発明者らは、以上のような要求がらα−シアノアクリ
レートモノマーのアニオン重合を防止する安定剤を研究
した結果、ホウフッ化水素酸（ＨＲＦ、、）が有効なア
ニオン重合防止剤であることを見出して本発明を完成し
たものである。<Means for Solving the Problems> As a result of research into stabilizers that prevent the anionic polymerization of α-cyanoacrylate monomers, the present inventors have found that hydroborofluoric acid (HRF) is effective. The present invention was completed by discovering that it is an anionic polymerization inhibitor.
すなわち本発明はα−シアノアクリレ−１〜千ツマ−１
００部（重量）に対して、ホウフッ化水素酸（ＩＩＢＦ
、）を１． Ｏ０％換算でＯ，０ＯＯ１，−０，５部（
重量）含有することを特徴とするα−シアノアクリレ−
１・系接着剤組成物である。That is, the present invention provides α-cyanoacrylate-1 to 1,000-1
00 parts (by weight), fluoroboric acid (IIBF
,) to 1. O,0OO1,-0,5 parts in O0% conversion (
α-cyanoacrylate characterized by containing (weight)
1. It is a type adhesive composition.
本発明のα−シアノアクリレート系接着剤組成物の主成
分であるα−シアノアクリレートモノマーはその代表的
なものとして、メチル−α−シアノアクリレート、エチ
ル−α−シアノアクリレート、プロピル−α−シアノア
クリレ−１〜、アリルα−シアノアクリレ−１〜、ブチ
ル−α−シアノ）？クリシー１〜、ヘプチル−α−シア
ノアクリレ−１・、ヘキシル−α−シアノアクリレ−１
〜、オクチル−α−シアノアクリレ−１・、デシル−α
−シアノアクリレート、ドデシル−α−シアノアクリレ
ート、（２−クロロエチル）−α−シアノアクリレ−１
〜、（２−メトキシエチル）−α−シアノアクリレート
、（２−エトキシエチル）−α−シアノアクリレ−１−
１（２−ブトキシエチル）−α−シアノアクリレート、
ベンジル−α−シアノアクリレート、フェニル−α−シ
アノアクリレート、１−リフルオロイソプロピル−α−
シアノアクリレート等が挙げられる。Representative examples of the α-cyanoacrylate monomer that is the main component of the α-cyanoacrylate adhesive composition of the present invention include methyl-α-cyanoacrylate, ethyl-α-cyanoacrylate, and propyl-α-cyanoacrylate. 1~, allyl α-cyanoacrylate-1~, butyl α-cyano)? chrysii 1~, heptyl-α-cyanoacrylate-1, hexyl-α-cyanoacrylate-1
~, octyl-α-cyanoacrylate-1, decyl-α
-cyanoacrylate, dodecyl-α-cyanoacrylate, (2-chloroethyl)-α-cyanoacrylate-1
~, (2-methoxyethyl)-α-cyanoacrylate, (2-ethoxyethyl)-α-cyanoacrylate-1-
1(2-butoxyethyl)-α-cyanoacrylate,
Benzyl-α-cyanoacrylate, Phenyl-α-cyanoacrylate, 1-lifluoroisopropyl-α-
Examples include cyanoacrylate.
本発明でいうホウフッ化水素Ｍ（ＨＢＦ、、）としては
、コニ業用及び試薬用として一般に供さオしている例え
ば３０〜４２％水溶液のものを使用することが出来る。As the hydrogen borofluoride M (HBF) referred to in the present invention, for example, a 30 to 42% aqueous solution, which is generally available for commercial use and reagent use, can be used.
ホウフッ化水ｍＷ＆（ＨＢＦ４）の添加量は、α−シア
ノアクリレ−１ヘモツマ−］、 Ｏ０部（重量）に対し
て、１００％換算で０．０００１〜０．５部（重量）、
好ましくは０．０００２〜０．０２部（重量）含有させ
ることにより目的とするα−シアノアクリレート系接着
剤組成物を得ることが出来る。この場合、従来がら公知
のＳ０２、ＳＯ３，パラトルエンスルホン酸、メタンス
ルホン酸、プロパンサルトンなどのアニオン重合防止剤
を併用することもできる。The amount of borofluoride water mW & (HBF4) added is 0.0001 to 0.5 part (weight) on a 100% basis, based on 0 parts (weight) of α-cyanoacryle-1 hemotsumer].
By containing preferably 0.0002 to 0.02 part (weight), the desired α-cyanoacrylate adhesive composition can be obtained. In this case, conventionally known anionic polymerization inhibitors such as S02, SO3, para-toluenesulfonic acid, methanesulfonic acid, and propane sultone can also be used.
又、本発明のα−シアノアクリレート系接着剤組成物に
は通常良く用いられているラジカル重合防止剤を併用添
加してもよい。ラジカル重合防止剤としてはハイドロキ
ノン、ハイドロキノンモノメチルエーテル、カテコール
、ピロガロールなどが有効である。Further, a commonly used radical polymerization inhibitor may be added to the α-cyanoacrylate adhesive composition of the present invention. Effective radical polymerization inhibitors include hydroquinone, hydroquinone monomethyl ether, catechol, and pyrogallol.
さらに又、増粘された接着剤組成物とする場合には、ポ
リメチルメタクリレ−１〜（ＰＭＭＡ）、ポリビニルア
セテ−１〜、セルロースアセテートイソブチレート、ア
クリルゴム、ポリウレタンなどが溶解される。その添加
量はα−シアノアクリレートに対して約１〜２０重量％
である。Furthermore, when preparing a thickened adhesive composition, polymethylmethacrylate-1~ (PMMA), polyvinyl acetate-1~, cellulose acetate isobutyrate, acrylic rubber, polyurethane, etc. are dissolved. The amount added is approximately 1 to 20% by weight based on α-cyanoacrylate.
It is.
他にセットタイムを短縮するための速硬化添加剤、接着
強度を高めるための添加剤、硬化した接着層に柔軟性を
付与するための可塑剤、耐衝撃性や剥離強度を付与する
ための飽和ポリエステル、耐熱性を付与するための改質
剤、塗布識別のための染料や顔料を添加することも可能
である。Other additives include fast curing additives to reduce set time, additives to increase adhesive strength, plasticizers to add flexibility to the cured adhesive layer, and saturation to add impact resistance and peel strength. It is also possible to add polyester, a modifier for imparting heat resistance, and dyes and pigments for coating identification.
具体的には、例えば、メトキシポリエチレングリコール
メタクリレート、１８−クラウン−６−エーテル、ガー
リック酸メトキシエチルエステルなどがあげられ、これ
らの添加量はα−シアノアクリレートモノマーに対して
０．０５〜１０重景％の置火で用いられる。Specifically, examples include methoxypolyethylene glycol methacrylate, 18-crown-6-ether, garlic acid methoxyethyl ester, etc., and the amount of these added is 0.05 to 10 times the α-cyanoacrylate monomer. Used in % fires.
〈発明の効果〉
本発明で用いるホウフッ化水素酸（Ｈｎ ｒｉう）は、
前記のとおり通常水溶液の形で取扱うことが出来るので
、従来のガス状の８０２やＨＦに比べて濃度調整が容易
であり、又ＢＦ３コンフプレックスのように発煙、着色
することがないという特徴を有する。<Effects of the invention> Hydrofluoroboric acid (Hnri) used in the present invention is
As mentioned above, since it can be handled in the form of an aqueous solution, it is easier to adjust the concentration compared to conventional gaseous 802 and HF, and it does not emit smoke or color unlike BF3 complex. .
本発明の接着剤組成物は、優れた貯蔵安定性を示すと同
時に、特に木材の接着に際しセットタイｌｌが速い特徴
を有している。The adhesive composition of the present invention exhibits excellent storage stability and at the same time is characterized by fast setting times, particularly when bonding wood.
〈実施例〉
以十に実施例及び比較例によって本発明を更に詳しく説
明する。文中、部とあるのは重量部を表わす。<Examples> The present invention will be explained in more detail below using Examples and Comparative Examples. In the text, parts refer to parts by weight.
実施例１〜９、比較例１〜９
エチル−α−シアノアクリレート１００部に、ハイドロ
キノン０．０５ｊ″？ｌＩを加え、さらにホウフッ化水
素酸（１−ＩＲＦ４）、Ｓｏ、、ＨＦ、ＢＦ３エーテル
コンプレックス（１３Ｆ＝’３・０（Ｃ２１−（５）２
）、メタンスルホン酸、ポリメチルメタクリレート（Ｐ
ＭＭＡ）、ポリウレタン、ポリエステル、アクリルエラ
ストマー、メトキシポリエチレングリコール（＃１００
０）メタクリレート、１８−クラウン６−エーテル、ピ
ロガロール、ガーリック酸エステルを表１に示す景添加
した。このようにして得られた接着剤について被接着材
マカバ／マカバ及び／又は鋼／鋼で、セットタイム試験
を行い、又ポリエチレン容器に充填し７０℃での加熱ゲ
ル化試験を行った結果は表１および表２に示す通りであ
った。Examples 1 to 9, Comparative Examples 1 to 9 To 100 parts of ethyl-α-cyanoacrylate, 0.05j″?lI of hydroquinone was added, and further fluoroboric acid (1-IRF4), So, HF, BF3 ether complex (13F='3・0(C21-(5)2
), methanesulfonic acid, polymethyl methacrylate (P
MMA), polyurethane, polyester, acrylic elastomer, methoxypolyethylene glycol (#100
0) Methacrylate, 18-crown 6-ether, pyrogallol, and garlic acid ester were added as shown in Table 1. The thus obtained adhesive was subjected to a set time test using Merkaba/Merkaba and/or steel/steel to be adhered, and was also filled into a polyethylene container and subjected to a heat gelling test at 70°C.The results are shown in Table 1. 1 and Table 2.
着色度はＪＩＳ Ｋ ４］、０１によるバーセン色数（
ＡＩ’１ｌＡ）で測定した。The degree of coloring is based on JIS K 4], Barsen color number according to 01 (
AI'11A).
また、接着試験は、ＩＪＳ Ｋ ６８６１に準拠して行
なった。Further, the adhesion test was conducted in accordance with IJS K 6861.
Claims (2)
）に対して、ホウフッ化水素酸を０．０００１〜０．５
部（重量）含有することを特徴とするα−シアノアクリ
レート系接着剤組成物。(1) Add 0.0001 to 0.5 parts of fluoroboric acid to 100 parts (weight) of α-cyanoacrylate monomer.
part (by weight) of an α-cyanoacrylate adhesive composition.
を併用する請求項（１）に記載のα−シアノアクリレー
ト系接着剤。(2) The α-cyanoacrylate adhesive according to claim (1), which uses methoxypolyethylene glycol methacrylate in combination.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2068680A JP2772442B2 (en) | 1989-03-24 | 1990-03-19 | Adhesive composition |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7274089 | 1989-03-24 | ||
| JP1-72740 | 1989-03-24 | ||
| JP2068680A JP2772442B2 (en) | 1989-03-24 | 1990-03-19 | Adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH037786A true JPH037786A (en) | 1991-01-14 |
| JP2772442B2 JP2772442B2 (en) | 1998-07-02 |
Family
ID=26409886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2068680A Expired - Fee Related JP2772442B2 (en) | 1989-03-24 | 1990-03-19 | Adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2772442B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002285107A (en) * | 1998-06-18 | 2002-10-03 | Closure Medical Corp | Stabilized monomer adhesive composition |
| JP2008179704A (en) * | 2007-01-25 | 2008-08-07 | Taoka Chem Co Ltd | 2-cyanoacrylate adhesive composition for mesh material |
| JP2008308647A (en) * | 2007-06-18 | 2008-12-25 | Taoka Chem Co Ltd | 2-cyanoacrylate adhesive composition for wood repair |
| JP2010174149A (en) * | 2009-01-29 | 2010-08-12 | Taoka Chem Co Ltd | 2-cyanoacrylate adhesive composition |
| JP2010189512A (en) * | 2009-02-17 | 2010-09-02 | Taoka Chem Co Ltd | 2-cyanoacrylate-based adhesive composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62100568A (en) * | 1985-10-26 | 1987-05-11 | Toagosei Chem Ind Co Ltd | Adhesive composition |
-
1990
- 1990-03-19 JP JP2068680A patent/JP2772442B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62100568A (en) * | 1985-10-26 | 1987-05-11 | Toagosei Chem Ind Co Ltd | Adhesive composition |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002285107A (en) * | 1998-06-18 | 2002-10-03 | Closure Medical Corp | Stabilized monomer adhesive composition |
| JP2008179704A (en) * | 2007-01-25 | 2008-08-07 | Taoka Chem Co Ltd | 2-cyanoacrylate adhesive composition for mesh material |
| JP2008308647A (en) * | 2007-06-18 | 2008-12-25 | Taoka Chem Co Ltd | 2-cyanoacrylate adhesive composition for wood repair |
| JP2010174149A (en) * | 2009-01-29 | 2010-08-12 | Taoka Chem Co Ltd | 2-cyanoacrylate adhesive composition |
| JP2010189512A (en) * | 2009-02-17 | 2010-09-02 | Taoka Chem Co Ltd | 2-cyanoacrylate-based adhesive composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2772442B2 (en) | 1998-07-02 |
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