JP4591727B2 - Curing accelerator - Google Patents
Curing accelerator Download PDFInfo
- Publication number
- JP4591727B2 JP4591727B2 JP30486999A JP30486999A JP4591727B2 JP 4591727 B2 JP4591727 B2 JP 4591727B2 JP 30486999 A JP30486999 A JP 30486999A JP 30486999 A JP30486999 A JP 30486999A JP 4591727 B2 JP4591727 B2 JP 4591727B2
- Authority
- JP
- Japan
- Prior art keywords
- curing accelerator
- odor
- curing
- hydroxy
- accelerator
- 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.)
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Description
【0001】
【発明の属する技術分野】
本発明は、α−シアノアクリレート系接着剤を急速に硬化させうる硬化促進剤に関し、特に低臭性でかつ硬化物の外観を損なうことのない速乾性の硬化促進剤に関する。
【0002】
【従来の技術】
α−シアノアクリレート系接着剤は、被着体表面に吸着されている微量の水分により急速にアニオン重合硬化して被着体同士を短時間で極めて強固に接着させることから、一液常温硬化型の瞬間接着剤として、金属、プラスチック、ゴム、木材などの接着に広く利用されている。
【0003】
一方、α−シアノアクリレート系接着剤は、接着部の隙間が大きい場合やはみ出した部分では硬化が極度に遅くなり、このことが原因となって白化現象を生じるという問題がある。かかる問題を解決する方法として、従来より硬化促進剤を使用する方法がとられてきた。
【0004】
硬化促進剤は、一般にα−シアノアクリレート系接着剤の硬化を促進するアミン化合物とこれを希釈する溶剤から構成されているが、これら成分の持つ臭気が作業環境上問題となっている。特に、促進剤組成の大部分(通常90%以上)を占める溶剤臭気の影響が大きい。
【0005】
特開昭59−66471には、促進剤の臭気を和らげる目的で沸点50〜250℃のアミン化合物、脱臭剤、溶剤からなる組成物が開示されている。脱臭剤はアミン化合物の臭気を緩和または脱臭する目的で添加されるが、溶剤の臭気まで緩和あるいは脱臭することはできない。
【0006】
特開平3−207779には、硬化物の白化を防ぐ目的で塩基性化合物、水可溶性有機溶剤、水からなる組成物が開示されているが、水は揮発性が低いため促進剤の乾燥性を悪くしてしまう。
【0007】
【発明が解決しようとする課題】
この発明の目的は、上述のような問題を解決しようとしてなされたもので、すなわち低臭性でかつ硬化物の外観を損なうことのない速乾性のα−シアノアクリレート系接着剤用硬化促進剤を提供しようとするものである。
【0008】
【課題を解決するための手段】
本発明者は、上記課題を解決するため鋭意検討した結果、上記課題が下記配合硬化促進剤により解決できることを見いだした。
【0009】
すなわち、本発明は下記(A)および(B)成分を含有する硬化促進剤により前述の課題を解決した。
(A)有機アミン化合物
(B)分子中にカルボニル基と水酸基を有するケトアルコール化合物
【0010】
この発明に使用できる(A)有機アミン化合物の具体例としては、トリエチルアミン、ジエチルアミン、イソプロピルアミン、ブチルアミン、トリブチルアミン等の脂肪族アミン類、N,N−ジメチルアニリン、N,N−ジエチルアニリン、N,N−ジメチル−o−トルイジン、N,N−ジメチル−m−トルイジン、N,N−ジメチル−p−トルイジン等の芳香族アミン類等が挙げられるが、特に芳香族三級アミンが好ましい。
【0011】
この発明に使用できる(B)ケトアルコール化合物とは、分子中にカルボニル基と水酸基の両方の官能基を有する化合物であり、具体例としてはヒドロキシアセトン、4−ヒドロキシ−2−ブタノン、3−ヒドロキシ−3−メチル−2−ブタノン、4−ヒドロキシ−4−メチル−2−ペンタノン等が挙げられる。これらのケトアルコール化合物は1種類でもよく、数種類を混合して使用してもよい。
【0012】
硬化促進剤中の(A)有機アミン化合物含有量は、0.1〜10重量%であることが好ましく、これよりも含有量が少ない場合は硬化促進効果が低下する。また、これよりも含有量が多い場合はアミン化合物の臭気が強くなってくる。
【0013】
さらに、本発明の硬化促進剤は他の(C)有機溶剤を含有することができる。具体例としては、メタノール、エタノール、プロパノール等のアルコール化合物、アセトン、メチルエチルケトン、ヘキサノン、シクロヘキサノン等のケトン化合物、酢酸メチル、酢酸エチル、ヘキシルアセテート、エチルカーボネート、エチレングリコールジアセテート等のエステル化合物、ヘキサン、シクロヘキサン、ペンタン等の脂肪族炭化水素化合物、トルエン、キシレン等の芳香族炭化水素化合物が挙げられ、単独でも数種類を混合して使用してもよい。なお、臭気や乾燥性の点からメタノール、エタノールなどの低級アルコールが特に好ましい。
【0014】
ただし、成分(A)、(B)および(C)を含有する硬化促進剤においては、(A)の含有量が0.1〜10重量%であり、かつ(A)と(B)の合計量が30重量%以上であることが好ましい。これよりも含有量が少ない場合は硬化物が白化する場合がある。
【0015】
この発明に係わる硬化促進剤は、低臭性でかつ硬化物の外観を損なうことのない速乾性の促進剤であり、α−シアノアクリレート系接着剤と併用して工業用、家庭用に広く使用できる。
【0016】
【発明の実施の形態】
以下に実施例および比較例を挙げてこの発明を説明するが、この発明はこれら実施例により限定されるものではない。
【0017】
【実施例1〜8】
(A)有機アミン化合物、(B)ケトアルコール化合物、(C)有機溶剤を表1に示す割合で配合した硬化促進剤を調製した。黒色のポリフェニレンオキサイド板上に、瞬間接着剤スリーボンド1783(スリーボンド社製)を塗布し、その上に本硬化促進剤を滴下した。その臭気と硬化物の外観の評価結果を表1に示す。
【0018】
【表1】
【0019】
硬化した瞬間接着剤は、ケトアルコール化合物が少ないとわずかに白っぽくなるが、適当量用いると無色透明となった。また、溶剤の臭気はほとんど感じられなかった。
【0020】
【比較例1〜4】
ケトアルコール化合物を添加しない硬化促進剤を表2に示す割合で調製し、実施例と同様に評価した。
【0021】
【表2】
【0022】
有機溶剤として低級アルコールを使用した場合、臭気は問題ないが硬化物は白化した。また、ケトアルコール化合物相当量(比較例4)のアセトンとメタノールの混合溶剤を使用しても硬化物は白化した。従って、ケトアルコール化合物とケトン/アルコール混合溶剤は、硬化物の白化性に関する作用が全く異なっていることがわかる。
【0023】
【発明の効果】
本発明のα−シアノアクリレート系接着剤用硬化促進剤は、低臭性であることから工業用としてばかりでなく、家庭用としても有効に使用される。また速乾性であることから、工程時間を短縮できる。さらに硬化物が白化しないことから、接着部が表面に出てしまうような製品の製造に使用することができる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a curing accelerator capable of rapidly curing an α-cyanoacrylate-based adhesive, and particularly to a quick-drying curing accelerator that has low odor and does not impair the appearance of a cured product.
[0002]
[Prior art]
α-Cyanoacrylate adhesive is a one-component room-temperature curing type because it adheres to adherends very quickly in a short time by rapid anionic polymerization curing with a small amount of moisture adsorbed on the adherend surface. As an instant adhesive, it is widely used for bonding metal, plastic, rubber, wood, etc.
[0003]
On the other hand, the α-cyanoacrylate-based adhesive has a problem that when the gap between the bonded portions is large or in the protruding portion, the curing is extremely slow, which causes a whitening phenomenon. As a method for solving such a problem, a method using a curing accelerator has been conventionally used.
[0004]
The curing accelerator is generally composed of an amine compound that accelerates curing of the α-cyanoacrylate adhesive and a solvent that dilutes the amine compound, but the odor of these components is a problem in the working environment. In particular, the influence of the solvent odor which occupies most of the accelerator composition (usually 90% or more) is large.
[0005]
JP-A-59-66471 discloses a composition comprising an amine compound having a boiling point of 50 to 250 ° C., a deodorizing agent and a solvent for the purpose of reducing the odor of the accelerator. The deodorizing agent is added for the purpose of reducing or deodorizing the odor of the amine compound, but it cannot reduce or deodorize the odor of the solvent.
[0006]
JP-A-3-207779 discloses a composition comprising a basic compound, a water-soluble organic solvent, and water for the purpose of preventing whitening of the cured product. However, since water is low in volatility, the drying property of the accelerator is reduced. It will be bad.
[0007]
[Problems to be solved by the invention]
An object of the present invention is to solve the above-described problems, that is, to provide a quick-drying curing accelerator for an α-cyanoacrylate adhesive that has low odor and does not impair the appearance of a cured product. It is something to be offered.
[0008]
[Means for Solving the Problems]
As a result of intensive studies to solve the above problems, the present inventor has found that the above problems can be solved by the following blended curing accelerator.
[0009]
That is, this invention solved the above-mentioned subject with the hardening accelerator containing the following (A) and (B) component.
(A) Organic amine compound (B) Keto alcohol compound having carbonyl group and hydroxyl group in the molecule
Specific examples of the (A) organic amine compound that can be used in the present invention include aliphatic amines such as triethylamine, diethylamine, isopropylamine, butylamine, and tributylamine, N, N-dimethylaniline, N, N-diethylaniline, N Aromatic amines such as N, N-dimethyl-o-toluidine, N, N-dimethyl-m-toluidine, N, N-dimethyl-p-toluidine, and the like.
[0011]
The (B) keto alcohol compound that can be used in the present invention is a compound having both a carbonyl group and a hydroxyl group in the molecule. Specific examples thereof include hydroxyacetone, 4-hydroxy-2-butanone, 3-hydroxy -3-methyl-2-butanone, 4-hydroxy-4-methyl-2-pentanone and the like. These ketoalcohol compounds may be used alone or in combination.
[0012]
The content of the organic amine compound (A) in the curing accelerator is preferably 0.1 to 10% by weight. When the content is lower than this, the curing acceleration effect is lowered. Moreover, when there is more content than this, the odor of an amine compound will become strong.
[0013]
Furthermore, the hardening accelerator of this invention can contain another (C) organic solvent. Specific examples include alcohol compounds such as methanol, ethanol, propanol, ketone compounds such as acetone, methyl ethyl ketone, hexanone, cyclohexanone, ester compounds such as methyl acetate, ethyl acetate, hexyl acetate, ethyl carbonate, ethylene glycol diacetate, hexane, Examples thereof include aliphatic hydrocarbon compounds such as cyclohexane and pentane, and aromatic hydrocarbon compounds such as toluene and xylene, and these may be used alone or in combination. In addition, lower alcohols such as methanol and ethanol are particularly preferable from the viewpoint of odor and dryness.
[0014]
However, in the curing accelerator containing components (A), (B) and (C), the content of (A) is 0.1 to 10% by weight, and the total of (A) and (B) The amount is preferably 30% by weight or more. When there is less content than this, hardened | cured material may whiten.
[0015]
The curing accelerator according to the present invention is a quick-drying accelerator that has low odor and does not impair the appearance of the cured product, and is widely used for industrial and household use in combination with an α-cyanoacrylate adhesive. it can.
[0016]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described with reference to examples and comparative examples, but the present invention is not limited to these examples.
[0017]
Examples 1-8
A curing accelerator was prepared by blending (A) an organic amine compound, (B) a ketoalcohol compound, and (C) an organic solvent in the proportions shown in Table 1. On the black polyphenylene oxide plate, instantaneous adhesive ThreeBond 1783 (manufactured by ThreeBond Co., Ltd.) was applied, and a main curing accelerator was dropped onto the adhesive. The evaluation results of the odor and the appearance of the cured product are shown in Table 1.
[0018]
[Table 1]
[0019]
The cured instant adhesive turned slightly whitish when the amount of ketoalcohol compound was small, but became colorless and transparent when used in an appropriate amount. Moreover, the odor of the solvent was hardly felt.
[0020]
[Comparative Examples 1-4]
Curing accelerators to which no ketoalcohol compound was added were prepared in the proportions shown in Table 2, and evaluated in the same manner as in the examples.
[0021]
[Table 2]
[0022]
When a lower alcohol was used as the organic solvent, the odor was not a problem but the cured product was whitened. Moreover, even if the mixed solvent of acetone and methanol of the keto alcohol compound equivalent amount (Comparative Example 4) was used, the cured product was whitened. Therefore, it can be seen that the keto alcohol compound and the ketone / alcohol mixed solvent have completely different effects on the whitening property of the cured product.
[0023]
【The invention's effect】
The α-cyanoacrylate adhesive curing accelerator of the present invention is effectively used not only for industrial use but also for home use because of its low odor. Moreover, since it is quick-drying, process time can be shortened. Furthermore, since a hardened | cured material does not whiten, it can be used for manufacture of the product from which an adhesion part comes out on the surface.
Claims (1)
(A)成分:ジアルキルアニリンおよび/またはジアルキルトルイジン
(B)成分:4−ヒドロキシ−2−ブタノン、3−ヒドロキシ−3−メチル−2−ブタノンおよび4−ヒドロキシ−4−メチル−2−ペンタノンから少なくとも1選択されるケトアルコール化合物
(C)成分:メタノールおよび/またはエタノール A dripping type curing accelerator dropped on an α-cyanoacrylate-based adhesive, characterized in that the following components ( A) to (C) are essential components and water is not added during the adjustment .
Component (A): dialkylaniline and / or dialkyltoluidine
Component (B): a keto alcohol compound selected from at least one selected from 4-hydroxy-2-butanone, 3-hydroxy-3-methyl-2-butanone and 4-hydroxy-4-methyl-2-pentanone
Component (C): methanol and / or ethanol
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30486999A JP4591727B2 (en) | 1999-10-27 | 1999-10-27 | Curing accelerator |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30486999A JP4591727B2 (en) | 1999-10-27 | 1999-10-27 | Curing accelerator |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2001123126A JP2001123126A (en) | 2001-05-08 |
JP4591727B2 true JP4591727B2 (en) | 2010-12-01 |
Family
ID=17938267
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP30486999A Expired - Fee Related JP4591727B2 (en) | 1999-10-27 | 1999-10-27 | Curing accelerator |
Country Status (1)
Country | Link |
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JP (1) | JP4591727B2 (en) |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2929113B2 (en) * | 1990-01-08 | 1999-08-03 | 東亞合成株式会社 | Curing accelerator composition for instant adhesive |
JPH08188748A (en) * | 1994-11-30 | 1996-07-23 | Sekisui Chem Co Ltd | Quick-setting adhesive composition |
-
1999
- 1999-10-27 JP JP30486999A patent/JP4591727B2/en not_active Expired - Fee Related
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JP2001123126A (en) | 2001-05-08 |
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