JPH02263880A - Adhesive composition - Google Patents

Adhesive composition

Info

Publication number
JPH02263880A
JPH02263880A JP8527589A JP8527589A JPH02263880A JP H02263880 A JPH02263880 A JP H02263880A JP 8527589 A JP8527589 A JP 8527589A JP 8527589 A JP8527589 A JP 8527589A JP H02263880 A JPH02263880 A JP H02263880A
Authority
JP
Japan
Prior art keywords
liquid
adhesive composition
peroxide
functional
liquids
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.)
Pending
Application number
JP8527589A
Other languages
Japanese (ja)
Inventor
Hideji Nunogami
布上 秀二
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daiabondo Kogyo Kk
Original Assignee
Daiabondo Kogyo Kk
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Daiabondo Kogyo Kk filed Critical Daiabondo Kogyo Kk
Priority to JP8527589A priority Critical patent/JPH02263880A/en
Publication of JPH02263880A publication Critical patent/JPH02263880A/en
Pending legal-status Critical Current

Links

Abstract

PURPOSE:To provide the subject non-toxic composition consisting of two kinds of liquid each containing a functional (meth)acrylate monomer and separately containing an organic peroxide and a cure accelerate in respective liquid, having high tensile strength, moderate curing time and high storage stability, free from metal corrosion and producible at a low cost. CONSTITUTION:The objective two-pack adhesive composition contains a functional (meth)acrylate in at least one of the liquid components and further contains (A) an organic peroxide such as benzoyl peroxide or methyl ethyl ketone peroxide in one liquid and (B) a cure accelerator composed of a phthalocyanine compound or porphyrin complex of a metal selected from Al, Ni, Co, Cu and Fe in the other liquid.

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は二液性アクリル反応型接着剤に関するものであ
る。
DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a two-component acrylic reactive adhesive.

(従来の技術) アクリル反応型接着剤の反応(硬化)機構としては、有
機過酸化物類や過安息香酸、過酢酸などを分解し、ラジ
カルを発生させ、アクリルモノマーを重合させて硬化さ
せるものが一般的であるが。
(Conventional technology) The reaction (curing) mechanism of acrylic reactive adhesives is to decompose organic peroxides, perbenzoic acid, peracetic acid, etc., generate radicals, and polymerize and cure acrylic monomers. Although it is common.

この硬化の促進剤として様々な方法が取られている。−
例を示せば、レドックス触媒系、アミン−アルデヒド縮
合物系、N−N’ジメチルアニリンなどのアニリン系、
ナンテン酸コバルト等の金属石鹸、ジメチルトルイジン
等のトルイジン系、チオウレア等のウレア系、メルカプ
トベンゾイミダゾール等のチオアミド系、鉄−ポリアミ
ン錯体等があげられる。
Various methods have been used as accelerators for this curing. −
Examples include redox catalyst systems, amine-aldehyde condensate systems, aniline systems such as N-N' dimethylaniline,
Examples include metal soaps such as cobalt nanthenate, toluidine-based soaps such as dimethyltoluidine, urea-based soaps such as thiourea, thioamide-based soaps such as mercaptobenzimidazole, and iron-polyamine complexes.

(発明が解決しようとする問題点) しかし、これらの硬化促進剤はそれぞれ一長一短があり
、−例を示せばN −N’ジメテルアニリン′は発ガン
性の可能性があり、アミン−アルデヒド縮合物fチオウ
レア系は酸の存在を必要条件とするため、金属に対し腐
食の問題がある。また、鉄−ポリアミン鰭体系は価格が
高いなどの難点があり、これらの問題点などを解決する
ことが要求されてきた。
(Problems to be Solved by the Invention) However, each of these curing accelerators has its advantages and disadvantages; for example, N -N'dimethylaniline' is potentially carcinogenic, and amine-aldehyde condensation Since thiourea-based compounds require the presence of an acid, there is a problem of corrosion to metals. Further, the iron-polyamine fin system has drawbacks such as high cost, and there has been a demand for solutions to these problems.

本発明に使用する硬化促進剤として、フタロシアニン化
合物またはポルフィリン錯体であって。
The curing accelerator used in the present invention is a phthalocyanine compound or a porphyrin complex.

アルミ、ニッケル、コバルト、銅及び鉄の群から選択さ
れた金属との化合物または錯体であることを特徴とし、
前記問題点を解決しようとしたものである。
Characterized by being a compound or complex with a metal selected from the group of aluminum, nickel, cobalt, copper and iron,
This is an attempt to solve the above problems.

(発明の構成) 以下2本発明の構成を具体的に説明する。(Structure of the invention) Two configurations of the present invention will be specifically explained below.

本発明の接着剤組成物は二液からなるものである。一方
の液には有機過酸化物または硬化促進剤のうちのいずれ
かを、また他方の液には残りを含有し、さらには少なく
とも一方の液には官能性の七ツマ−を含有し、このほか
に非官能性モノマーオリゴマーや種々の重合体(共重合
体を含む)などをも包含するものである。
The adhesive composition of the present invention consists of two components. One solution contains either the organic peroxide or the curing accelerator, the other solution the remainder, and at least one solution contains the functional heptamine. It also includes non-functional monomer oligomers and various polymers (including copolymers).

該官能性モノマーとしては、アクリル酸、メタクリル酸
、2−ヒドロキシエチルメタクリレート等の、ヒドロキ
シアルキルメタクリレート、ジメチルアミノエチルメタ
クリレート等のジアルキルアミノエチルメタクリレート
、エチレングリコールジメタクリレート等の七ノ〜ポリ
エチレングリコールジメタクリレート、トリメチロール
プロパントリアクリレート、グリシジルメタクリレート
等をあげることができる。
The functional monomers include acrylic acid, methacrylic acid, hydroxyalkyl methacrylates such as 2-hydroxyethyl methacrylate, dialkylaminoethyl methacrylates such as dimethylaminoethyl methacrylate, hepta-polyethylene glycol dimethacrylates such as ethylene glycol dimethacrylate, Examples include trimethylolpropane triacrylate and glycidyl methacrylate.

非官能性モノマーとしては、メチルメタクリレート等の
C1〜C1sのアルキルメタクリレートがあげられる。
Examples of non-functional monomers include C1-C1s alkyl methacrylates such as methyl methacrylate.

オリゴマーとしては、ウレタンアクリレート。The oligomer is urethane acrylate.

エポキシアクリレート、ポリエステルアクリレート等が
あげられる。
Examples include epoxy acrylate and polyester acrylate.

重合体としては、ポリメタクリル酸エステル。The polymer is polymethacrylic acid ester.

ポリアクリル酸エステル、ポリスチレン、ABS樹脂、
ポリビニルクロリド、各種合成ゴム、ポリエステル樹脂
等があげられる。
Polyacrylic ester, polystyrene, ABS resin,
Examples include polyvinyl chloride, various synthetic rubbers, and polyester resins.

前述の有機過酸化物は重合開始剤であり、該物質として
は過酸化ペンゾール、メチルエチルケトンパーオキサイ
ド、シクロヘキサノンパーオキサイド、クメンハイドロ
パーオキサイド、t−ブチA/ハイドロパーオキサイド
、ジーt−7’ f /L/ ハイドロパーオキサイド
、ジクミルパーオキサイド。
The aforementioned organic peroxide is a polymerization initiator, and examples of the substance include penzole peroxide, methyl ethyl ketone peroxide, cyclohexanone peroxide, cumene hydroperoxide, t-butyA/hydroperoxide, and di-t-7'f/ L/ Hydroperoxide, dicumyl peroxide.

テトラメチルハイドロパーオキサイド等があげられる。Examples include tetramethyl hydroperoxide.

また、前述の硬化促進剤は1重合・硬化を促進するもの
であって、アルミ、ニッケル、コバルト。
Further, the above-mentioned curing accelerator is one that promotes monopolymerization and curing, and includes aluminum, nickel, and cobalt.

銅及び鉄の群から選択された金属と7タロシアニン、ま
たはポルフィリンとの化合物または錯体である。
It is a compound or complex of a metal selected from the group of copper and iron and a 7-talocyanine or a porphyrin.

このような構成からなる本発明の接着剤組成物は以下の
ような多くの利点、特徴を有するものである。
The adhesive composition of the present invention having such a structure has many advantages and characteristics as described below.

1、接着強度が大である。1. High adhesive strength.

2、使用時において、二液の混合を必要としない(もち
ろん二液を混合して使用してもかまわない)。
2. There is no need to mix the two liquids during use (of course, the two liquids may be used in combination).

3、酸を使用しな(ても硬化するので金属に対しての腐
食がない。
3. Do not use acid (it hardens even if you use it, so there is no corrosion to metals).

4、貯蔵安定性がよ(、常温で貯蔵できる。4. Good storage stability (Can be stored at room temperature.

5.7タロシアニン系の金属化合物は着色顔料として上
布されており、毒性もなく1価格も廉価である。
5.7 Talocyanine-based metal compounds are used as coloring pigments on textiles, and are non-toxic and inexpensive.

(実施例) 以下1本発明を実施例によってさらに詳述するが2本発
明はこれら実施例に限定されるものではない。
(Examples) Hereinafter, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to these examples.

表1に示すような配合組成の接着剤を作成し。An adhesive having the composition shown in Table 1 was prepared.

二液をA剤、B剤としそれぞれA−1,A−2,B−1
,B−2の四つの組成のものを作成し、接着試験を行っ
た。
The two liquids are A-1, A-2, and B-1 respectively.
, B-2 were prepared and an adhesion test was conducted.

接着試験は硬化時間及び引張りせん断強度を測定し、そ
の結果を表2に示した。接着試験は下記の方法たよって
行った。
In the adhesion test, curing time and tensile shear strength were measured, and the results are shown in Table 2. The adhesion test was conducted according to the following method.

(1)硬化時間二表面をトリクロルエチレンで脱脂した
厚さ1.6m、幅25fl、長さ100n+の冷間圧延
鋼板を用意する。該鋼板に本発明接着剤組成物のA液及
びB液をそれぞれ別々に塗布し1次いでこれらを接合し
く接合長さ250)、接合部が手で引き剥がせなくなる
までの時間を測定し、硬化時間とする。
(1) Hardening time 2. Prepare a cold rolled steel plate with a thickness of 1.6 m, a width of 25 fl, and a length of 100 n+ whose surface has been degreased with trichlorethylene. Liquids A and B of the adhesive composition of the present invention were applied separately to the steel plate, and then these were bonded to a bonding length of 250 mm. The time until the bonded portion could no longer be peeled off by hand was measured and cured. Time.

(2)引張りせん断強度:該鋼板を(1)のように接合
しく接合長さ12.5wx ) 、室温で24時間放置
後、引張りせん断強度を測定した。測定はテンシロン引
張り試験機(東洋ボールドウィン裏)を用い。
(2) Tensile shear strength: The steel plates were joined as in (1) and the joint length was 12.5wx), and after being left at room temperature for 24 hours, the tensile shear strength was measured. Measurements were made using a Tensilon tensile tester (manufactured by Toyo Baldwin).

引張り速度5 m/mで行った。The tensile speed was 5 m/m.

表1 実施配合例1 表2 硬化時間及び引張りせん断強度 本発明に用いる該硬化触媒は、接着剤配合比ぶで0.1
〜2.0 %であることが望ましい。すなわち。
Table 1 Practical formulation example 1 Table 2 Curing time and tensile shear strength The curing catalyst used in the present invention has an adhesive formulation ratio of 0.1
It is desirable that the content is between 2.0% and 2.0%. Namely.

0.1S未満にしたときはほとんど硬化しないかもしく
は硬化時間が長(、また、  2.0%以上配合しても
硬化時間は早くならない。これらB−3よりB−δ迄の
種々に配合した実施例を表3に示す。
If it is less than 0.1S, it will hardly cure or the curing time will be long (and even if it is added in an amount of 2.0% or more, the curing time will not become faster. Examples are shown in Table 3.

表3 実施配合例2 (発明の効果) 実施例の表にみるように本発明の接着剤組成物は引張り
強度にも優れており、硬化時間も使用し易い範囲内を示
すものであり、接着剤としての性能も優れたものである
Table 3 Practical Formulation Example 2 (Effects of the Invention) As seen in the table of Examples, the adhesive composition of the present invention has excellent tensile strength, and the curing time is within a range that is easy to use. It also has excellent performance as an agent.

また、二液の混合を必要とせず、酸を使わな(ても硬化
するので金属に対する腐食もなく、貯蔵安定性がよく、
毒性がなく9価格も低床であるという経済性9作業性そ
の他にも大きな利点、効果を有するものである。
In addition, it does not require the mixing of two liquids, does not require the use of acids (it hardens even when used, so it does not corrode metals, and has good storage stability.
It has other great advantages and effects, such as being non-toxic, low cost, economical and easy to work with.

Claims (3)

【特許請求の範囲】[Claims] (1)二液からなる接着剤において、その二液のうち少
なくとも一方の液は官能性のアクリレートモノマーおよ
び/またはメタクリレートモノマーを含有し、また一方
の液には有機過酸化物または硬化促進剤のうちのいずれ
かを含有し、他方の液には残りを含有する接着剤組成物
(1) In a two-part adhesive, at least one of the two parts contains a functional acrylate monomer and/or methacrylate monomer, and one part contains an organic peroxide or a curing accelerator. An adhesive composition containing one of the liquids, and the other liquid containing the remaining liquid.
(2)一方の液に含有する硬化促進剤はフタロシアニン
化合物であって、アルミ、ニッケル、コバルト、銅及び
鉄の群から選択された金属との化合物であることを特徴
とする請求項(1)記載の接着剤組成物。
(2) Claim (1) characterized in that the curing accelerator contained in one of the liquids is a phthalocyanine compound, and is a compound with a metal selected from the group of aluminum, nickel, cobalt, copper, and iron. Adhesive composition as described.
(3)一方の液に含有する硬化促進剤はポルフィリン錯
体であって、アルミ、ニッケル、コバルト、銅及び鉄の
群から選択された金属との錯体であることを特徴とする
請求項(1)記載の接着剤組成物。
(3) Claim (1) characterized in that the curing accelerator contained in one of the liquids is a porphyrin complex, and is a complex with a metal selected from the group of aluminum, nickel, cobalt, copper, and iron. Adhesive composition as described.
JP8527589A 1989-04-04 1989-04-04 Adhesive composition Pending JPH02263880A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP8527589A JPH02263880A (en) 1989-04-04 1989-04-04 Adhesive composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP8527589A JPH02263880A (en) 1989-04-04 1989-04-04 Adhesive composition

Publications (1)

Publication Number Publication Date
JPH02263880A true JPH02263880A (en) 1990-10-26

Family

ID=13854013

Family Applications (1)

Application Number Title Priority Date Filing Date
JP8527589A Pending JPH02263880A (en) 1989-04-04 1989-04-04 Adhesive composition

Country Status (1)

Country Link
JP (1) JPH02263880A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07150113A (en) * 1993-11-29 1995-06-13 Okura Ind Co Ltd Two-pack acrylic adhesive for assembling precision mating component and assembling of precision mating component therewith
CN1088083C (en) * 1997-03-28 2002-07-24 国家淀粉及化学投资控股公司 Rapid curing structural acrylic adhesive
WO2012092034A3 (en) * 2010-12-28 2012-09-20 Dura Chemicals, Inc. Additives for curable liquid compositions
GB2497114A (en) * 2011-12-01 2013-06-05 Spinnaker Int Ltd Anaerobic adhesive compositions
DE102013222278A1 (en) * 2013-11-01 2015-05-07 Tesa Se Reactive 2-component adhesive system
JP2017512875A (en) * 2014-04-01 2017-05-25 テーザ・ソシエタス・ヨーロピア Attaching method by starting plasma
CN105705601B (en) * 2013-11-01 2018-06-01 德莎欧洲股份公司 Reactive two component adhesive system

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54158444A (en) * 1978-06-03 1979-12-14 Kyoritsu Kagaku Sangyo Adhesive composition
JPS5516018A (en) * 1978-07-19 1980-02-04 Denki Kagaku Kogyo Kk Acrylate curing composition
JPS5569672A (en) * 1978-11-06 1980-05-26 Usm Corp Adhesive and its activating agent
JPS63232568A (en) * 1988-03-11 1988-09-28 Toshiba Corp Original reader
JPS63232569A (en) * 1987-03-19 1988-09-28 Canon Inc Data communication equipment

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54158444A (en) * 1978-06-03 1979-12-14 Kyoritsu Kagaku Sangyo Adhesive composition
JPS5516018A (en) * 1978-07-19 1980-02-04 Denki Kagaku Kogyo Kk Acrylate curing composition
JPS5569672A (en) * 1978-11-06 1980-05-26 Usm Corp Adhesive and its activating agent
JPS63232569A (en) * 1987-03-19 1988-09-28 Canon Inc Data communication equipment
JPS63232568A (en) * 1988-03-11 1988-09-28 Toshiba Corp Original reader

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07150113A (en) * 1993-11-29 1995-06-13 Okura Ind Co Ltd Two-pack acrylic adhesive for assembling precision mating component and assembling of precision mating component therewith
CN1088083C (en) * 1997-03-28 2002-07-24 国家淀粉及化学投资控股公司 Rapid curing structural acrylic adhesive
WO2012092034A3 (en) * 2010-12-28 2012-09-20 Dura Chemicals, Inc. Additives for curable liquid compositions
CN103403091A (en) * 2010-12-28 2013-11-20 杜拉化学制品有限公司 Additives for curable liquid compositions
US10696863B2 (en) 2010-12-28 2020-06-30 Dura Chemicals, Inc. Additives for curable liquid compositions
US9976054B2 (en) 2010-12-28 2018-05-22 Dura Chemicals, Inc. Additives for curable liquid compositions
EA027701B1 (en) * 2010-12-28 2017-08-31 Дура Кемикалс, Инк. Air-drying composition (embodiments), method for forming a coating and curable composition (embodiments)
CN103403091B (en) * 2010-12-28 2016-11-16 杜拉化学制品有限公司 Additive for curable liquid composition
GB2497114A (en) * 2011-12-01 2013-06-05 Spinnaker Int Ltd Anaerobic adhesive compositions
GB2497114B (en) * 2011-12-01 2015-02-18 Spinnaker Int Ltd Adhesive composition
US20160264823A1 (en) * 2013-11-01 2016-09-15 Tesa Se Reactive 2-component adhesive system
KR20160082526A (en) * 2013-11-01 2016-07-08 테사 소시에타스 유로파에아 Reactive 2-component adhesive system
JP2016539218A (en) * 2013-11-01 2016-12-15 テーザ・ソシエタス・ヨーロピア Two-component reactive adhesive system
CN105705601A (en) * 2013-11-01 2016-06-22 德莎欧洲公司 Reactive 2-component adhesive system
US9834707B2 (en) 2013-11-01 2017-12-05 Tesa Se Reactive 2-component adhesive system
WO2015062809A1 (en) * 2013-11-01 2015-05-07 Tesa Se Reactive 2-component adhesive system
CN105705601B (en) * 2013-11-01 2018-06-01 德莎欧洲股份公司 Reactive two component adhesive system
TWI649390B (en) * 2013-11-01 2019-02-01 特薩股份有限公司 Reactive 2-component adhesive system, manufacturing method and use thereof
DE102013222278A1 (en) * 2013-11-01 2015-05-07 Tesa Se Reactive 2-component adhesive system
JP2017512875A (en) * 2014-04-01 2017-05-25 テーザ・ソシエタス・ヨーロピア Attaching method by starting plasma

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