JPH0481632B2 - - Google Patents
Info
- Publication number
- JPH0481632B2 JPH0481632B2 JP59231100A JP23110084A JPH0481632B2 JP H0481632 B2 JPH0481632 B2 JP H0481632B2 JP 59231100 A JP59231100 A JP 59231100A JP 23110084 A JP23110084 A JP 23110084A JP H0481632 B2 JPH0481632 B2 JP H0481632B2
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- cyanoacrylate
- adhesive composition
- adhesive strength
- powder
- 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 - Lifetime
Links
- 239000000853 adhesive Substances 0.000 claims description 37
- 230000001070 adhesive effect Effects 0.000 claims description 37
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 239000004677 Nylon Substances 0.000 claims description 7
- 229920001778 nylon Polymers 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 241000283690 Bos taurus Species 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- 210000004268 dentin Anatomy 0.000 description 3
- 229910001651 emery Inorganic materials 0.000 description 3
- 229920000298 Cellophane Polymers 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 238000007718 adhesive strength test Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003479 dental cement Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
Description
産業上の利用分野
本発明はα−シアノアクリレートを主成分とす
る接着剤組成物に関する。
従来技術
α−シアノアクリレートは、一般に瞬間接着剤
としてよく知られているものである。該接着剤は
短時間で強力な接着力が得られるため、工業的に
も医学的にも広く使用されている。しかし、嫌気
性接着剤であるため、表面を大気に露出して使用
し難く、また強力な接着力が得られる皮膜厚さに
限度があり、数十ないし数百ミクロン以上の空間
を充てんして接着するという用途には使用できな
かつた。
発明の目的
本発明は、α−シアノアクリレートを使用し
て、大気中でも安定して適用でき、かつ厚い塗膜
としても強力な接着力を発揮する接着剤組成物、
特に歯科用に適した接着剤組成物を提供すること
を目的とする。
発明の構成
本発明の接着剤組成物は、(イ)α−シアノアクリ
レートと(ロ)Ｎ−含有ビニルモノヤー又はＮ−含有
ポリマーを併含するものである。
上記ビニルモノマーとしては、下記一般式
（）〜（）で表される化合物の少なくとも一
種が用いられ、
（ただし、R1はＨ又はCH3、R2はＨ又は炭素数
１〜５のアルキル基を示す。）
（ただし、ＲはＨ又はCH3を示す。）
また、Ｎ−含有ポリマーとしては、各種ナイロ
ン樹脂、例えば６−ナイロン、6.6−ナイロン、
6.10−ナイロン、メトキシメチル化ナイロン等が
用いられる。
α−シアノアクリレートと前記(ロ)の物質の併用
割合は特に限定されないが、一般に重量比率で
99.5：0.5〜50：50であるのが好ましく、特に
95：５〜60：40であるのがよい。
なお、Ｎ−含有ポリマーは80メツシユ以下の細
かい微粉末状で使用するのが好ましく、特に200
メツシユより細かい微粉末を使用するのが効果的
である。
かかる本発明の接着剤組成物は、大気中でも安
定して使用でき、しかも数百ミクロン以上という
厚い層状に適用しても、強力な接着力を得ること
ができるが、これは(ロ)の物質がα−シアノアクリ
レートの反応触媒として働くと同時に充てん剤及
び接着剤としての効果をも発揮するためと思われ
る。
本発明の接着剤組成物には、更に他の化合物が
添加されてもよいが、該添加物はＮ−含有の粉体
物質であるのが好ましく、また接着剤組成物中20
重量％を越えない範囲で使用されるべきである。
実施例
(1) 牛歯エナメル質又は象牙質を＃240αエメリ
ーペーパーで研磨後、リン酸処理又は10−３処
理（クエン酸10％と塩化第二鉄３％の水溶液を
用いたクリーニング）した表面に第１表記載の
13種の接着剤を適用して接着強度試験を行なつ
た。その結果を第１表に示すが、測定値は接着
物を37℃の水中に24時間浸漬した後のものであ
る。
（接着強度試験）
試験体（牛歯象牙質又はエナメル質）の表面
に、中央に直径５mmの穴をあけた１cm角のセロ
フアンテープを貼着し、該セロフアンテープ上
に穴を覆つて接着剤を盛り上げ、アクリル棒を
接着し、引張試験をして、試験体と直径５mmの
範囲で接着する接着剤の接着強度を測定する。
INDUSTRIAL APPLICATION FIELD The present invention relates to an adhesive composition containing α-cyanoacrylate as a main component. Prior Art α-cyanoacrylate is generally well known as an instant adhesive. Since this adhesive can provide strong adhesive force in a short time, it is widely used both industrially and medically. However, because it is an anaerobic adhesive, it is difficult to use with the surface exposed to the atmosphere, and there is a limit to the thickness of the film that can provide strong adhesive strength, so it cannot be used to fill spaces larger than tens or hundreds of microns. It could not be used for gluing purposes. Purpose of the Invention The present invention provides an adhesive composition using α-cyanoacrylate that can be stably applied even in the atmosphere and exhibits strong adhesive strength even as a thick coating.
The object is to provide an adhesive composition particularly suitable for dental use. Structure of the Invention The adhesive composition of the present invention contains (a) α-cyanoacrylate and (b) an N-containing vinyl monolayer or an N-containing polymer. As the vinyl monomer, at least one of the compounds represented by the following general formulas () to () is used, (However, R1 represents H or CH3 , and R2 represents H or an alkyl group having 1 to 5 carbon atoms.) (However, R represents H or CH3 .) In addition, as the N-containing polymer, various nylon resins, such as 6-nylon, 6.6-nylon,
6.10-Nylon, methoxymethylated nylon, etc. are used. The proportion of α-cyanoacrylate and the substance (b) above is not particularly limited, but it is generally expressed in terms of weight ratio.
99.5:0.5 to 50:50 is preferable, especially
The ratio should be between 95:5 and 60:40. The N-containing polymer is preferably used in the form of a fine powder of 80 mesh or less, especially 200 mesh or less.
It is effective to use a finer powder than mesh. The adhesive composition of the present invention can be used stably even in the atmosphere, and even when applied to a thick layer of several hundred microns or more, it can obtain strong adhesive strength, but this is because the substance (b) This is thought to be because it functions as a reaction catalyst for α-cyanoacrylate and at the same time exhibits effects as a filler and adhesive. Although other compounds may be added to the adhesive composition of the present invention, the additives are preferably N-containing powder materials, and the additives are preferably N-containing powder materials.
It should be used within a range not exceeding % by weight. Example (1) Surface of bovine tooth enamel or dentin polished with #240α emery paper and then treated with phosphoric acid or 10-3 treatment (cleaning using an aqueous solution of 10% citric acid and 3% ferric chloride) as listed in Table 1.
Adhesive strength tests were conducted using 13 types of adhesives. The results are shown in Table 1, and the measured values are after the adhesive was immersed in water at 37°C for 24 hours. (Adhesion strength test) A 1 cm square cellophane tape with a 5 mm diameter hole in the center was attached to the surface of the test specimen (bovine dentin or enamel), and the hole was covered with the cellophane tape. The adhesive is piled up, an acrylic rod is attached, and a tensile test is performed to measure the adhesive strength of the adhesive that adheres to the test piece within a 5 mm diameter range.
【表】
(2) 牛歯エナメル質を＃240エメリーペーパーで
研磨後、リン酸処理した表面に第２表に記載す
る３種の接着剤を適用して前記(1)と同様の方法
で接着強度を測定した。その結果を第２表に示
す。[Table] (2) After polishing bovine tooth enamel with #240 emery paper, apply the three types of adhesives listed in Table 2 to the phosphoric acid-treated surface and adhere in the same manner as in (1) above. The strength was measured. The results are shown in Table 2.
【表】
(3) 牛歯象牙質を＃240エメリーペーパーで研磨
後、リン酸処理又は10−３処理（クエン酸10％
と塩化第二鉄３％の水溶液を用いたクリーニン
グ）した表面に第３表に示す６種の接着剤を適
用した前記(1)と同様の方法で接着強度を測定し
た。その結果を第３表に示す。[Table] (3) After polishing bovine dentin with #240 emery paper, phosphoric acid treatment or 10-3 treatment (citric acid 10%
The adhesive strength was measured in the same manner as in (1) above, in which the six types of adhesives shown in Table 3 were applied to the surface which had been cleaned using a 3% aqueous solution of ferric chloride. The results are shown in Table 3.
【表】
これらの結果から明らかなように、本発明の接
着剤（表１のNo.１〜10、表２のNo.１及び表３のNo.
１、３）はいずれも市販の接着剤表３のNo.５）に
比して著しく優れた接着性を示すものであり、ま
た、α−シアノアクリレート単独使用の場合（表
１のNo.11、12、表２のNo.２及び表３のNo.２、４）
と比較してもほぼ同等又はそれ以上の接着強度を
示すものである。
更に、α−シアノアクリレートは嫌気性接着剤
であり、大気に露出したり、塗布量が多くなると
十分な接着強度を得られないなど、均一な接着強
度を得難く、適用範囲が限られるのに対し、本発
明の接着剤は常に安定して優れた接着強度を示す
表３のNo.１〜４参照）。
発明の効果
本発明の接着剤組成物は、触媒及び充てん剤と
して働くと同時に、それ自身も接着剤として機能
しうる可能性のある特殊なポリマー及び／又はモ
ノマーを、α−シアノアクリレートに添加混合し
ているため、α−シアノアクリレート単独使用の
場合と何ら遜色のない接着力を有し、しかも厚い
層状に適用したり、大気に露出した状態で使用し
ても同様に優れた接着力を示す。従つて、α−シ
アノアクリレートを従来使用し難いとされていた
歯科用接着剤組成物にも広く使用できるものと
し、また電子部品の表面保護膜の形成などにも使
用できるものとした。[Table] As is clear from these results, the adhesives of the present invention (Nos. 1 to 10 in Table 1, No. 1 in Table 2, and No. 1 in Table 3)
1 and 3) both exhibit significantly superior adhesion compared to commercially available adhesive No. 5) in Table 3, and when α-cyanoacrylate is used alone (No. 11 in Table 1). , 12, No. 2 in Table 2 and No. 2, 4 in Table 3)
Even when compared to the above, it shows almost the same or higher adhesive strength. Furthermore, α-cyanoacrylate is an anaerobic adhesive, and if it is exposed to the atmosphere or applied in a large amount, it will not be able to obtain sufficient adhesive strength, making it difficult to obtain uniform adhesive strength and limiting its range of application. On the other hand, the adhesive of the present invention always shows stable and excellent adhesive strength (see Nos. 1 to 4 in Table 3). Effects of the Invention The adhesive composition of the present invention has a special polymer and/or monomer that acts as a catalyst and a filler, and at the same time has the potential to function as an adhesive itself. As a result, it has an adhesive strength that is comparable to that of α-cyanoacrylate alone, and it also shows the same excellent adhesive strength even when applied in a thick layer or when exposed to the atmosphere. . Therefore, α-cyanoacrylate can be widely used in dental adhesive compositions, which were conventionally considered difficult to use, and can also be used in forming protective films on the surfaces of electronic components.
Claims (1)
（〜）で表されるＮ−含有ビニルモノマーの
少なくとも一種を、重量比率で99.5：0.5〜50：
50の割合で含むことを特徴とする接着剤組成物。 （ただし、R1はＨ又はCH3、R2はＨ又は炭素数
１〜５のアルキル基を示す。） （ただし、ＲはＨ又はCH3を示す。） ２ (イ)α−シアノアクリレートと、(ロ)Ｎ−含有ポ
リマーであるナイロン樹脂の粉末を、重量比率で
99.5：0.5〜50：50の割合で含むことを特徴とす
る接着剤組成物。 ３ 上記ナイロン樹脂粉末が80メツシユ以下の微
粉末であることを特徴とする請求項２の接着剤組
成物。[Scope of Claims] 1 (a) α-cyanoacrylate and (b) at least one N-containing vinyl monomer represented by the following general formula (~) in a weight ratio of 99.5:0.5 to 50:
Adhesive composition characterized in that it contains in a proportion of 50. (However, R1 represents H or CH3 , and R2 represents H or an alkyl group having 1 to 5 carbon atoms.) (However, R represents H or CH3 .) 2. (a) α-cyanoacrylate and (b) powder of nylon resin, which is an N-containing polymer, in weight ratios.
An adhesive composition comprising: 99.5:0.5 to 50:50. 3. The adhesive composition according to claim 2, wherein the nylon resin powder is a fine powder of 80 mesh or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59231100A JPS61108684A (en) | 1984-10-31 | 1984-10-31 | Adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59231100A JPS61108684A (en) | 1984-10-31 | 1984-10-31 | Adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61108684A JPS61108684A (en) | 1986-05-27 |
| JPH0481632B2 true JPH0481632B2 (en) | 1992-12-24 |
Family
ID=16918293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59231100A Granted JPS61108684A (en) | 1984-10-31 | 1984-10-31 | Adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61108684A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001253870A (en) * | 2000-03-13 | 2001-09-18 | Manac Inc | Method for producing imide compound and its new derivative |
| JP5071606B2 (en) * | 2001-04-24 | 2012-11-14 | 株式会社スリーボンド | Alpha-cyanoacrylate-containing photocurable resin composition |
-
1984
- 1984-10-31 JP JP59231100A patent/JPS61108684A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61108684A (en) | 1986-05-27 |
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