JPS63207877A - Adhesive composition of methyleneimide type - Google Patents
Adhesive composition of methyleneimide typeInfo
- Publication number
- JPS63207877A JPS63207877A JP4015787A JP4015787A JPS63207877A JP S63207877 A JPS63207877 A JP S63207877A JP 4015787 A JP4015787 A JP 4015787A JP 4015787 A JP4015787 A JP 4015787A JP S63207877 A JPS63207877 A JP S63207877A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formulas
- adhesive composition
- methyleneimine
- compounds
- 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
Links
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 41
- 239000000853 adhesive Substances 0.000 title claims abstract description 37
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical group N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004793 Polystyrene Substances 0.000 claims abstract description 11
- 229920002223 polystyrene Polymers 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- -1 benzylmethyleneimine Chemical class 0.000 abstract description 12
- 229920003048 styrene butadiene rubber Polymers 0.000 abstract description 7
- HROUEPWZUPHWDY-UHFFFAOYSA-N 2-phenylethanimine Chemical compound N=CCC1=CC=CC=C1 HROUEPWZUPHWDY-UHFFFAOYSA-N 0.000 abstract description 4
- 238000002156 mixing Methods 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- KEXBVUYXPSSCAX-UHFFFAOYSA-N cyclohexylmethanimine Chemical compound N=CC1CCCCC1 KEXBVUYXPSSCAX-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- CDOJUCGFHYNQKY-UHFFFAOYSA-N 3-phenylpropan-1-imine Chemical compound N=CCCC1=CC=CC=C1 CDOJUCGFHYNQKY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- TVXLUCDRBUBWSG-UHFFFAOYSA-N (4-methylcyclohexyl)methanimine Chemical compound CC1CCC(C=N)CC1 TVXLUCDRBUBWSG-UHFFFAOYSA-N 0.000 description 1
- FHCXNGSACYKFGQ-UHFFFAOYSA-N 2-(3-methylphenyl)ethanimine Chemical compound CC1=CC=CC(CC=N)=C1 FHCXNGSACYKFGQ-UHFFFAOYSA-N 0.000 description 1
- REEOBCWAKKXIDT-UHFFFAOYSA-N 2-(4-methylphenyl)ethanimine Chemical compound CC1=CC=C(CC=N)C=C1 REEOBCWAKKXIDT-UHFFFAOYSA-N 0.000 description 1
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 1
- BKMWOINKWLGJGH-UHFFFAOYSA-N 2-phenylpropan-1-imine Chemical compound N=CC(C)C1=CC=CC=C1 BKMWOINKWLGJGH-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000004830 Super Glue Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、メチレンイミン系接着剤組成物、さらに詳し
くは、特に瞬間接着性に優れた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 a methyleneimine adhesive composition, and more particularly to an adhesive composition particularly excellent in instant adhesive properties.
モノメチレンイミン化合物、およびビスメチレンイミン
化合物は、１個の３級窒素に１個のメチレン基が付加し
た化合物であり、大気中のわずかな水分で重合固化する
性質を有することがら、接着剤、特に瞬間接着剤として
の応用が知られている。Monomethyleneimine compounds and bismethyleneimine compounds are compounds in which one methylene group is added to one tertiary nitrogen, and because they have the property of polymerizing and solidifying with a small amount of moisture in the atmosphere, they are used as adhesives, In particular, it is known for its application as an instant adhesive.
しかし、これらのモノメチレンイミン化合物、およびビ
スメチレンイミン化合物は、各種被着体を瞬間的に接着
できるものの、その接着力は実用上において満足できる
ものではなく、改質等の改良が必要である。However, although these monomethyleneimine compounds and bismethyleneimine compounds can instantaneously bond various adherends, their adhesive strength is not satisfactory for practical use, and improvements such as modification are required. .
モノメチレンイミン化合物、およびビスメチレンイミン
化合物は、大気中のわずかな水分で容易に重合し、重合
物を生成するが重合に伴う体積収縮率が１０％以上ある
こと、ならびに重合体が、硬くて脆い等の欠点を有して
いる。Monomethyleneimine compounds and bismethyleneimine compounds easily polymerize with a small amount of moisture in the air to form a polymer, but the volume shrinkage rate associated with polymerization is 10% or more, and the polymer is hard and It has disadvantages such as brittleness.
そのため、各種被着体を瞬間的に接着できるものの、そ
の接着力は、実用上において満足できるものではなく、
改良が必要である。Therefore, although various adherends can be bonded instantaneously, the adhesive strength is not satisfactory for practical use.
Improvement is needed.
本発明者らは鋭意検討の結果、モノメチレンイミン化合
物およびビスメチレンイミン化合物は、ポリスチレンま
たは、スチレンとブタジェンの共重合体と相溶性がよく
、常温にて容易に混合溶解できることから、これらの少
なくとも１種類を、モノメチレンイミン化合物およびビ
スメチレンイミン化合物のそれぞれ単独または混合物（
以下「メチレンイミン化合物」と略記する。）に配合、
溶解させることにより接着力が飛躍的に向上し、かつ良
好な瞬間接着性を有するようになることを見出し、本発
明を完成した。As a result of extensive studies, the present inventors found that monomethyleneimine compounds and bismethyleneimine compounds have good compatibility with polystyrene or a copolymer of styrene and butadiene, and can be easily mixed and dissolved at room temperature. One type is a monomethyleneimine compound and a bismethyleneimine compound, each alone or in a mixture (
Hereinafter, it will be abbreviated as "methyleneimine compound". ),
The present invention was completed based on the discovery that the adhesive strength was dramatically improved by dissolving the adhesive, and the adhesive had good instantaneous adhesive properties.
ここでいうモノメチレンイミン化合物とは次の一般式Ｃ
Ｉ）、〔■］で表される化合物である。The monomethyleneimine compound mentioned here has the following general formula C
I), a compound represented by [■].
（：Ｉ） ｃｕ］
（式中、Ｒ１は水素原子またはメチル基を、Ｒ２はメチ
ル基を、ｎは、１〜２の整数を、ｍはＯまたは１〜３の
整数をそれぞれ表わす。）
代表的なモノメチレンイミン化合物としては、ベンジル
メチレンイミン、フェネチルメチレンイミン、α−メチ
ルベンジルメチレンイミン、３−メチルベンジルメチレ
ンイミン、４−メチルベンジルメチレンイミン、シクロ
へキシルメチレンイミン、４−メチルシクロヘキシルメ
チレンイミンを例示することができる。(:I) cu] (In the formula, R1 represents a hydrogen atom or a methyl group, R2 represents a methyl group, n represents an integer of 1 to 2, and m represents O or an integer of 1 to 3.) Representative Examples of monomethyleneimine compounds include benzylmethyleneimine, phenethylmethyleneimine, α-methylbenzylmethyleneimine, 3-methylbenzylmethyleneimine, 4-methylbenzylmethyleneimine, cyclohexylmethyleneimine, 4-methylcyclohexylmethyleneimine. can be exemplified.
ビスメチレンイミン化合物とは、次の一般式〔■〕、（
ＩＶ）および〔Ｖ〕で表わされる化合物である。Bismethyleneimine compounds have the following general formula [■], (
IV) and [V].
（式中、Ｒ２はメチル基を、ｍはＯまたは１〜３の整数
をそれぞれ表わす。）
代表的なビスメチレンイミン化合物としては、５−メチ
レンイミノ−１，３，３−）ツメチル−１−メチレンイ
ミノメチルシクロヘキサン、５−メチレンイミノ−２，
２，４−）ジメチル−１−メチレンイミノメチルシクロ
ペンタン、■、２−ビス（メチレンイミノ）シクロヘキ
サンを例示することができる。(In the formula, R2 represents a methyl group, and m represents O or an integer of 1 to 3.) Typical bismethyleneimine compounds include 5-methyleneimino-1,3,3-)trimethyl-1- Methyleneiminomethylcyclohexane, 5-methyleneimino-2,
Examples include 2,4-)dimethyl-1-methyleneiminomethylcyclopentane and (1),2-bis(methyleneimino)cyclohexane.
これらのモノメチレンイミン化合物またはビスメチレン
イミン化合物は、それぞれ単独で用いても、あるいは混
合物として用いてもよい。These monomethyleneimine compounds or bismethyleneimine compounds may be used alone or as a mixture.
ポリスチレン、またはスチレンとブタジェンの共重合体
の少なくとも１種類の添加量は、メチレンイミン化合物
１００重量部に対して、１〜２５重量部、好ましくは５
〜２０重量部が望ましい。The amount of polystyrene or at least one copolymer of styrene and butadiene added is 1 to 25 parts by weight, preferably 5 parts by weight, based on 100 parts by weight of the methyleneimine compound.
~20 parts by weight is desirable.
上記範囲以上の添加量では、メチレンイミン化合物の濃
度が低くなりすぎ、瞬間接着性が不十分となり、上記範
囲以下の添加量では、接着力の向上効果がみられない。If the amount added is above the above range, the concentration of the methyleneimine compound will be too low, resulting in insufficient instant adhesiveness, and if the amount added is below the above range, no effect of improving adhesive strength will be observed.
メチレンイミン化合物の貯蔵安定性向上のためメチレン
イミン化合物に有機リチウムとシクロヘキシルメチレン
イミンを添加することが知られているが（特開昭６Ｏ−
１４６８５９）、本発明においても、これらの安定剤を
添加することも可能である。It is known that organic lithium and cyclohexylmethyleneimine are added to methyleneimine compounds in order to improve their storage stability (JP-A No. 6 O-
146859), it is also possible to add these stabilizers in the present invention.
本発明によれば、接着性能の向上したメチレンイミン系
瞬間接着剤組成物が得られる。According to the present invention, a methyleneimine-based instant adhesive composition with improved adhesive performance can be obtained.
すなわち、メチレンイミン化合物にポリスチレンまたは
スチレンとブタジェンの共重合体を添加することにより
、メチレンイミン化合物の重合に伴う体積収縮が緩和さ
れ、さらに可とう性が賦与され、その結果接着力が向上
する。That is, by adding polystyrene or a copolymer of styrene and butadiene to the methyleneimine compound, volumetric shrinkage accompanying polymerization of the methyleneimine compound is alleviated, and flexibility is imparted, resulting in improved adhesive strength.
本発明で得られる接着剤組成物は、鉄、銅、アルミニウ
ム等の金属類、スチレン−ブタジェン共重合体、ポリメ
チルメタクリレート、ポリ塩化ビニール、ポリカーボネ
ート等のゴム、プラスチック類、木材、紙等を瞬間的に
接着し、しかもこれまでのメチレンイミン化合物に比べ
て接着力が著しく向上している。The adhesive composition obtained in the present invention can be used to instantly bond metals such as iron, copper, and aluminum, rubbers such as styrene-butadiene copolymers, polymethyl methacrylate, polyvinyl chloride, and polycarbonate, plastics, wood, paper, etc. Furthermore, the adhesive strength is significantly improved compared to conventional methyleneimine compounds.
また、接着作業時および接着後においても、刺激臭はな
く、被着体の変色も認められない。Furthermore, there is no irritating odor and no discoloration of the adherend is observed during or after bonding.
以下に、実施例および比較例を示して本発明を具体的に
説明する。The present invention will be specifically explained below by showing Examples and Comparative Examples.
接着作業および接着後の養生は温度２０〜２５°Ｃ１相
対湿度４０〜６０％の条件下で行なった。The bonding work and curing after bonding were carried out at a temperature of 20 to 25° C. and a relative humidity of 40 to 60%.
引張りせん断接着試験は、接着後２−４時間養生した後
実施した。Tensile shear adhesion tests were performed after curing for 2-4 hours after adhesion.
なお、実施例および比較例における引張りせん断接着強
さ、セットタイムの測定は、ＪＩＳ Ｋ６８６１−１
９７７ （α−シアノアクリレート系接着剤試験方法）
に準拠しておこなった。The tensile shear adhesive strength and set time in the Examples and Comparative Examples were measured in accordance with JIS K6861-1.
977 (α-cyanoacrylate adhesive test method)
This was done in accordance with.
また、実施例、比較例中「部ｊは、重量部を表わす。Furthermore, in Examples and Comparative Examples, "part j" represents parts by weight.
実施例 １
ベンジルメチレンイミン５０部と５−メチレンイミノ−
１，３，３，−トリメチル−１−メチレンイミノ−メチ
ルシクロヘキサン５０部の混合物にポリスチレン（昭和
電工株式会社製 ニスブライト ハイフロー２）を１０
部混合、溶解させ均一な透明溶液を得た。Example 1 50 parts of benzylmethyleneimine and 5-methyleneimino
10 parts of polystyrene (Nisbright High Flow 2, manufactured by Showa Denko K.K.) was added to a mixture of 50 parts of 1,3,3,-trimethyl-1-methyleneimino-methylcyclohexane.
The mixture was mixed and dissolved to obtain a homogeneous clear solution.
この接着剤組成物を用い、鋼板（ＪＩＳ Ｇ３１４１−
３ＰＣＣ−ＳＢ）を被着体として用いて、接着試験を行
なった。Using this adhesive composition, a steel plate (JIS G3141-
An adhesion test was conducted using 3PCC-SB) as an adherend.
その結果、セットタイムは、３０〜６０秒となり、良好
な瞬間接着性を有することがわかった。As a result, the set time was 30 to 60 seconds, and it was found that the film had good instant adhesive properties.
一方、引張りせん断接着強さは、４．５ＭＰａとなり、
比較例１のポリスチレンを配合しない場合に比べて接着
力が著しく向上した。On the other hand, the tensile shear adhesive strength was 4.5 MPa,
Adhesive strength was significantly improved compared to Comparative Example 1 in which polystyrene was not blended.
また、接着作業時および接着後において、刺激臭は感じ
られなかった。Further, no irritating odor was detected during or after the bonding process.
実施例 ２
実施例１に示したメチレンイミン化合物の混合物１００
部にスチレン−ブタジェン共重合体（旭化成工業株式会
社製 タフプレンＡ）を１０部、混合、溶解させて均一
な透明液体を得た。Example 2 Mixture 100 of methyleneimine compounds shown in Example 1
10 parts of a styrene-butadiene copolymer (Tuffrene A, manufactured by Asahi Kasei Industries, Ltd.) were mixed and dissolved therein to obtain a uniform transparent liquid.
この接着剤組成物を用いて、実施例１と同様の条件で接
着試験を行なった。An adhesion test was conducted using this adhesive composition under the same conditions as in Example 1.
その結果、セットタイムは、３０〜６０秒となり、良好
な瞬間接着性を有することがわかった。As a result, the set time was 30 to 60 seconds, and it was found that the film had good instant adhesive properties.
引張りせん断接着強さは、４．７ＭＰａとなり比較例１
および比較例２に比べて著しく向上することがわかった
。The tensile shear adhesive strength was 4.7 MPa, which was Comparative Example 1.
It was found that this was significantly improved compared to Comparative Example 2.
実施例 ３
実施例１で用いたメチレンイミン化合物の混合物にｎ−
ブチルリチウムおよびシクロヘキシルメチレンイミンを
それぞれ２００ｐｐｍおよび３゜１ｗｔ％添加し、貯蔵
安定性を改良したメチレンイミン化合物１００部にスチ
レン−ブタジェン共重合体（旭化成工業株式会社製 タ
フブレンＡ）を７部、混合溶解させて均一な透明液体を
得た。Example 3 The mixture of methyleneimine compounds used in Example 1 was added with n-
Mix and dissolve 7 parts of styrene-butadiene copolymer (Toughblane A manufactured by Asahi Kasei Corporation) into 100 parts of a methyleneimine compound to which 200 ppm and 3.1 wt% of butyllithium and cyclohexylmethyleneimine have been added to improve storage stability. A homogeneous transparent liquid was obtained.
この接着剤組成物を用いて、実施例工と同様の条件で接
着試験を行った。Using this adhesive composition, an adhesion test was conducted under the same conditions as in the example.
その結果、セットタイムは、３０〜６０秒、引張りせん
断接着強さは、４．３ＭＰａであった。As a result, the set time was 30 to 60 seconds, and the tensile shear adhesive strength was 4.3 MPa.
実施例 ４〜７
第１表に示すメチレンイミン化合物とポリスチレンまた
はスチレン−ブタジェン共重合体の配合により、いずれ
も均一で透明な液体を得た。Examples 4 to 7 Uniform and transparent liquids were obtained by blending the methyleneimine compounds shown in Table 1 with polystyrene or styrene-butadiene copolymers.
これらの接着剤組成物を用いて、実施例１と同様の方法
により、セットタイムおよび引張りせん断接着強さを測
定した。その結果を第１表に示した。Using these adhesive compositions, set time and tensile shear adhesive strength were measured in the same manner as in Example 1. The results are shown in Table 1.
比較例 １
実施例１において、ポリスチレンを配合しないメチレン
イミン化合物を接着剤として用いて、実施例１と同様に
セットタイムおよび引張りせん断接着強さを測定した。Comparative Example 1 In Example 1, a methyleneimine compound containing no polystyrene was used as an adhesive, and the set time and tensile shear adhesive strength were measured in the same manner as in Example 1.
その結果は、それぞれ３０〜６０秒、および２．０ＭＰ
ａであった。The results are 30-60 seconds and 2.0MP respectively
It was a.
比較例 ２
実施例２に示した組成物において、スチレン−ブタジェ
ン共重合体（旭化成工業株式会社製 タフブレンＡ）の
添加量を３０部とした接着剤組成物を用いて、実施例１
と同様の方法でセットタイムおよび引張りせん断接着強
さを測定した。Comparative Example 2 Example 1 was prepared by using an adhesive composition in which the composition shown in Example 2 had a styrene-butadiene copolymer (Toughblane A manufactured by Asahi Kasei Corporation) added in an amount of 30 parts.
Set time and tensile shear adhesive strength were measured in the same manner as described above.
その結果はそれぞれ３分以上、および１． ０ＭＰａで
あった。The results are 3 minutes or more and 1. It was 0 MPa.
比較例 ３
ベンジルメチレンイミン５０部と５−メチレンイミノ−
１，３，３，−）ツメチル−１−メチレンイミノメチル
シクロヘキサフ５０部の混合物にｎ−ブチルリチウムお
よびシクロへキシルメチレンイミンをそれぞれ２００ｐ
ｐｍおよび３．１ｗｔ％添加し、貯蔵安定性を向上させ
たメチレンイミン接着剤組成物を用いて、比較例１と同
様の方法で、セットタイムおよび引張りせん断接着強さ
を測定した。その結果はそれぞれ３０〜６０秒、および
２．２ＭＰａであった。Comparative Example 3 50 parts of benzylmethyleneimine and 5-methyleneimino
200 p each of n-butyllithium and cyclohexylmethyleneimine were added to a mixture of 50 parts of 1,3,3,-)methyl-1-methyleneiminomethylcyclohexaf.
Set time and tensile shear adhesive strength were measured in the same manner as in Comparative Example 1 using a methyleneimine adhesive composition containing 3.1 wt% of pm and 3.1 wt% to improve storage stability. The results were 30-60 seconds and 2.2 MPa, respectively.
比較例 ４〜７
第２表に示したメチレンイミン化合物、もしくはメチレ
ンイミン化合物とポリスチレンの接着剤組成物を用い、
第２表に示した被着体について比較例１と同様の方法で
セットタイムおよび引張りせん断接着強さを測定した。Comparative Examples 4 to 7 Using the methyleneimine compound shown in Table 2 or the adhesive composition of the methyleneimine compound and polystyrene,
The set time and tensile shear adhesive strength of the adherends shown in Table 2 were measured in the same manner as in Comparative Example 1.
その結果をまとめて第２表に示す。The results are summarized in Table 2.
第１表
木上記メチレンイミン化合物の略号は、次の化合物を表
わす。Table 1 The abbreviations for the methyleneimine compounds above represent the following compounds.
１） ＢＭＩ ： ベンジ）ジメチレンイミン２
） ＭＢＭ■： ４−メチルペンシルメチレンイミン
３） ＰＭＩ ： フェネチルメチレンイミン４
） Ｂｌｐ ： ５−メチレンイミノ−１，３，
３−）ジメチル−１−メチレンイミノメチルシクロヘキ
サン５） ＢＣｐ ： ５−メチレンイミノ−２
，２，５−トリメチル−１−メチレンイミノメチルシク
ロペンタン６） ＢＣｈ ： １，３−ビス（メ
チレンイミハーシクロヘキサシ第２表
木上記メチレンイミン化合物の略号は、次の化合物を表
わす。1) BMI: Bendi) dimethyleneimine 2
) MBM■: 4-methylpencylmethyleneimine 3) PMI: phenethylmethyleneimine 4
) Blp: 5-methyleneimino-1,3,
3-) Dimethyl-1-methyleneiminomethylcyclohexane 5) BCp: 5-methyleneimino-2
, 2,5-trimethyl-1-methyleneiminomethylcyclopentane 6) BCh: 1,3-bis(methyleneiminomethylcyclohexacyl) The abbreviations of the above methyleneimine compounds represent the following compounds.
Claims (1)
ン化合物、および一般式〔III〕、〔IV〕、〔Ｖ〕で表
わされるビスメチレンイミン化合物のそれぞれ単独、ま
たは混合物１００重量部に対し、ポリスチレン、または
スチレンとブタジエンの共重合体の少なくとも１種類を
１〜２５重量部配合してなるメチレンイミン系接着剤組
成物 ▲数式、化学式、表等があります▼〔 I 〕 ▲数式、化学式、表等があります▼〔II〕 ▲数式、化学式、表等があります▼〔III〕 ▲数式、化学式、表等があります▼〔IV〕 ▲数式、化学式、表等があります▼〔Ｖ〕 （式中、Ｒ＿１は水素原子またはメチル基を、Ｒ＿２は
メチル基を、ｎは、１〜２の整数を、ｍは０または１〜
３の整数をそれぞれ表わす。）[Scope of Claims] Monomethyleneimine compounds represented by general formulas [I] and [II], and bismethyleneimine compounds represented by general formulas [III], [IV], and [V], each singly or as a mixture. A methyleneimine adhesive composition containing 1 to 25 parts by weight of at least one type of polystyrene or a copolymer of styrene and butadiene per 100 parts by weight ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ [I] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [II] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [III] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [IV] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [ V] (In the formula, R_1 is a hydrogen atom or a methyl group, R_2 is a methyl group, n is an integer of 1 to 2, and m is 0 or 1 to
Each represents an integer of 3. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4015787A JPS63207877A (en) | 1987-02-25 | 1987-02-25 | Adhesive composition of methyleneimide type |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4015787A JPS63207877A (en) | 1987-02-25 | 1987-02-25 | Adhesive composition of methyleneimide type |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63207877A true JPS63207877A (en) | 1988-08-29 |
Family
ID=12572930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4015787A Pending JPS63207877A (en) | 1987-02-25 | 1987-02-25 | Adhesive composition of methyleneimide type |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63207877A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011500768A (en) * | 2007-10-24 | 2011-01-06 | ロックタイト （アール アンド ディー） リミテッド | Active methylene reagent and curable composition produced therefrom |
-
1987
- 1987-02-25 JP JP4015787A patent/JPS63207877A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011500768A (en) * | 2007-10-24 | 2011-01-06 | ロックタイト （アール アンド ディー） リミテッド | Active methylene reagent and curable composition produced therefrom |
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