JPS6220580A - Adhesive composition - Google Patents
Adhesive compositionInfo
- Publication number
- JPS6220580A JPS6220580A JP15958485A JP15958485A JPS6220580A JP S6220580 A JPS6220580 A JP S6220580A JP 15958485 A JP15958485 A JP 15958485A JP 15958485 A JP15958485 A JP 15958485A JP S6220580 A JPS6220580 A JP S6220580A
- Authority
- JP
- Japan
- Prior art keywords
- polyamine
- adhesive composition
- epoxyalkylalkoxysilane
- reaction product
- composition
- 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 12
- 239000000853 adhesive Substances 0.000 title claims description 14
- 230000001070 adhesive effect Effects 0.000 title claims description 14
- 229920000768 polyamine Polymers 0.000 claims abstract description 21
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 4
- 229920000570 polyether Polymers 0.000 claims abstract description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims abstract description 3
- 125000003827 glycol group Chemical group 0.000 claims description 2
- 239000011342 resin composition Substances 0.000 abstract description 5
- 229920005989 resin Polymers 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- -1 4-epoxycyclohexyl Chemical group 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229920006311 Urethane elastomer Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- SLQTWNAJXFHMHM-UHFFFAOYSA-N dimethoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(OC)OC)CCC2OC21 SLQTWNAJXFHMHM-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は密着剤組成物、更に詳しくは、各種樹脂組成物
の密着耐久性を向上せしめるためこれに添加する密着剤
組成物に関する。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to an adhesive composition, and more particularly to an adhesive composition that is added to various resin compositions in order to improve their adhesion durability.
従来技術と解決すべき問題点
通常、接着剤、ツーリング材、塗料、注入剤などの樹脂
組成物は、その密着力を向上させるため密着剤が添加配
合されている。かかる密着剤として、フェノール樹脂、
石油樹脂、エポキシ樹脂、シランカップリング剤、チタ
ネートカップリング剤等が用いられているが、特に密着
耐久性に満足な結果が得られず、他方下地へのプライマ
ー塗布により密着力を高める方法もとられているが、こ
れは作業省力化の上で好ましくない。Prior Art and Problems to be Solved Usually, adhesives are added to resin compositions such as adhesives, tooling materials, paints, and injection agents in order to improve their adhesion. Such adhesives include phenolic resin,
Petroleum resins, epoxy resins, silane coupling agents, titanate coupling agents, etc., have been used, but they have not produced satisfactory results in terms of adhesion durability, and methods of increasing adhesion by applying a primer to the base have been proposed. However, this is not desirable in terms of labor saving.
本発明者らは、広汎な樹脂組成物に対して適用でき、所
望の密着力（特に密着耐久性）を付与しうる密着剤を提
供するため鋭意研究を進めたところ、特定のエポキシ基
を有するアルコキシシラン化合物と１分子内に２個以上
のアミノ基を有する化合物との反応生成物が所期目的の
密着付与効果を発揮しうろことを見出し、本発明を完成
させるに至った。The present inventors conducted extensive research in order to provide an adhesive that can be applied to a wide range of resin compositions and can provide desired adhesion (particularly adhesion durability), and found that it has a specific epoxy group. The present inventors have discovered that a reaction product of an alkoxysilane compound and a compound having two or more amino groups in one molecule can exert the desired adhesion imparting effect, and have completed the present invention.
発明の構成と効果
すなわち、本発明は、エポキシアルキルアルコキシシラ
ンとポリアミンとの反応生成物から成ることを特徴とす
る密着剤組成物を提供するものである。Structure and Effects of the Invention That is, the present invention provides an adhesive composition characterized by comprising a reaction product of an epoxyalkylalkoxysilane and a polyamine.
本発明における上記エポキシアルキルアルコキシシラン
としては、例えばγ−グリシドキシブロピルジメチルエ
トキンンラン、γ−グリノドキシプロビルメチルノエト
キンンラン、γ−グリシドキンプロピルトリメトキンシ
ラン、β−（３，４−エポキシシクロヘキシル）エチル
トリメトキシノラン、β−（３，４−エポキシシクロヘ
キシル）エチルメチルジメトキンシランなどが挙げられ
る。Examples of the epoxyalkylalkoxysilane in the present invention include γ-glycidoxypropyldimethylethquinane, γ-glycidoxypropylmethylnoetquinane, γ-glycidoxypropyltrimethynesilane, β-(3, Examples include 4-epoxycyclohexyl)ethyltrimethoxynolane and β-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane.
本発明における上記ポリアミンとしては、例えばジエチ
レントリアミン、ジエチルアミノプロピルアミン、トリ
エチレンテトラミンなどの脂肪族ポリアミン、該脂肪族
ポリアミンをビスフェノールＡなどで変性した変性脂肪
族ポリアミン、ジアミノジフェニルメタン、ジアミノジ
フェニルスルホン、ベンジジンなどの芳香族ポリアミン
、該芳香族ポリアミンにモノエポキシなどをアダクトし
た変性芳香族ポリアミン、３．３′−ジメチル−４゜４
°−ジアミノーンシクロヘキシルメタンなどの指環式ポ
リアミン、上記脂肪族ポリアミンとダイマー酸を反応し
て得られるポリアミドアミン、これらのポリアミンとエ
チレンオキシド、プロピレンオキシドのようなアルキレ
ンオキノドを反応して得られる脂肪族ポリエーテルポリ
アミンなどが挙げられる。特に、ポリプロピレングリコ
ールを骨格とする脂肪族ポリエーテルポリアミンが好ま
しい。Examples of the above-mentioned polyamines in the present invention include aliphatic polyamines such as diethylenetriamine, diethylaminopropylamine, and triethylenetetramine, modified aliphatic polyamines obtained by modifying the aliphatic polyamines with bisphenol A, etc., diaminodiphenylmethane, diaminodiphenylsulfone, and benzidine. Aromatic polyamine, modified aromatic polyamine obtained by adducting monoepoxy or the like to the aromatic polyamine, 3.3'-dimethyl-4゜4
°-diaminone Cyclic polyamines such as cyclohexylmethane, polyamide amines obtained by reacting the above aliphatic polyamines with dimer acids, and fats obtained by reacting these polyamines with alkylene oxides such as ethylene oxide and propylene oxide. Examples include group polyether polyamines. Particularly preferred is an aliphatic polyether polyamine having a polypropylene glycol skeleton.
上記エポキシアルキルアルコキシシランとポリアミンの
反応は、両者の割合を化学量論的にほぼ当量となるよう
に設定し、これらを適当な溶剤（トルエン、キシレンな
どの芳香族系、酢酸エチル、酢酸ブチルなどのエステル
系）に混合した希釈溶液状態で、常温乃至加熱（４０〜
６０°Ｃ）下にて２０時間以上の条件で行えばよい。In the reaction of the above-mentioned epoxyalkylalkoxysilane and polyamine, the ratio of the two is set to be approximately equivalent stoichiometrically, and they are mixed in an appropriate solvent (aromatic type such as toluene, xylene, ethyl acetate, butyl acetate, etc.). in a diluted solution state mixed with ester type) at room temperature or heated (40~
60° C.) for 20 hours or more.
このようにして得られる反応生成物をそのまま本発明の
密着剤組成物として使用することができ、これを固形分
換算で各種の樹脂組成物１００部（重量部、以下同様）
に対し、通常０．１〜２０部の範囲で添加することによ
り、浸れた密着力（特に水中下の密着耐久性）を付与し
うろことが認められる。The reaction product obtained in this way can be used as it is as the adhesive composition of the present invention, and this can be added to 100 parts (parts by weight, same hereinafter) of various resin compositions in terms of solid content.
However, when added in an amount of usually 0.1 to 20 parts, it has been found that the adhesion strength (particularly the adhesion durability under water) can be improved.
次に実施例および比較例を挙げて本発明をより具体的に
説明する。Next, the present invention will be explained in more detail with reference to Examples and Comparative Examples.
実施例１〜８
表１に示す部数のエポキシアルキルアルコキシシラン（
チッソ社製、サイラエースＳ−５１０，−５２０）、ポ
リアミン（三井石油化学エポキシ社製、エポミゾクＱ−
６０４，−６３１，−６４０，−６９１）およびトルエ
ンを密閉容器に入れ、５０°Ｃで２４時間反応させて（
なお、ｒＲにてエポキノ基および第２級アミノ基の吸収
の消失を確認して、反応の終了とする）、密着剤組成物
を得る。Examples 1 to 8 Epoxyalkylalkoxysilane in the numbers shown in Table 1 (
Chisso Corporation, Sila Ace S-510, -520), Polyamine (Mitsui Petrochemical Epoxy Co., Ltd., Epomizoku Q-
604, -631, -640, -691) and toluene in a sealed container and reacted at 50°C for 24 hours (
Note that the reaction is terminated by confirming the disappearance of absorption of the epochino group and the secondary amino group by rR), and an adhesive composition is obtained.
密着試験
ウレタンゴム系接着剤（大日本インキ化学工業（株）製
、バンデソクスＴ−５２０５）をトルエン／メチルエチ
ルケトン混合溶剤で固形分１５％となるように希釈溶解
し、この１００部に固形分換算で実施例１の密着剤組成
物１部を添加したものを、Ｚｎ鋼板とＰＶＣンートの積
層接着に用いて評価する。この場合、常態強度は４．Ｏ
ｋｇ／２５ｍｍであった。Adhesion test A urethane rubber adhesive (manufactured by Dainippon Ink & Chemicals Co., Ltd., Bandesox T-5205) was diluted and dissolved in a mixed solvent of toluene/methyl ethyl ketone to a solid content of 15%, and 100 parts of this was dissolved in terms of solid content. A product to which 1 part of the adhesive composition of Example 1 was added was used for lamination adhesion between a Zn steel plate and a PVC sheet, and evaluated. In this case, the normal strength is 4. O
kg/25mm.
Claims (1)
の反応生成物から成ることを特徴とする密着剤組成物。 ２、ポリアミンが、ポリプロピレングリコールを骨格と
する脂肪族ポリエーテルポリアミンである前記第１項記
載の密着剤組成物。[Scope of Claims] 1. An adhesive composition comprising a reaction product of an epoxyalkylalkoxysilane and a polyamine. 2. The adhesive composition according to item 1 above, wherein the polyamine is an aliphatic polyether polyamine having a polypropylene glycol skeleton.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15958485A JPS6220580A (en) | 1985-07-18 | 1985-07-18 | Adhesive composition |
| US06/886,152 US4791214A (en) | 1985-07-18 | 1986-07-16 | Bonding agent and resin composition |
| KR1019860005786A KR870001280A (en) | 1985-07-18 | 1986-07-16 | Manufacturing method of binder and resin composition containing same |
| DE8686109821T DE3683417D1 (en) | 1985-07-18 | 1986-07-17 | ADHESIVES AND RESIN MIXTURE. |
| AU60275/86A AU590298B2 (en) | 1985-07-18 | 1986-07-17 | Bonding agent resin composition |
| EP86109821A EP0209851B1 (en) | 1985-07-18 | 1986-07-17 | Bonding agent and resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15958485A JPS6220580A (en) | 1985-07-18 | 1985-07-18 | Adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6220580A true JPS6220580A (en) | 1987-01-29 |
| JPH0454713B2 JPH0454713B2 (en) | 1992-09-01 |
Family
ID=15696905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15958485A Granted JPS6220580A (en) | 1985-07-18 | 1985-07-18 | Adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6220580A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8536294B2 (en) | 2004-09-02 | 2013-09-17 | The Yokohama Rubber Co., Ltd. | Adhesive composition |
| JP2022538726A (en) * | 2019-05-15 | 2022-09-06 | ダウ グローバル テクノロジーズ エルエルシー | Two-component adhesive composition, article prepared therewith, and method of preparation thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5294353A (en) * | 1976-02-04 | 1977-08-08 | Kansai Paint Co Ltd | Production of silica-resin composite |
| JPS60115619A (en) * | 1983-11-28 | 1985-06-22 | Toray Silicone Co Ltd | Thermosetting epoxy resin composition |
| JPS60215087A (en) * | 1984-04-10 | 1985-10-28 | Nissan Motor Co Ltd | Adhesive for fixing vehicle inside mirror |
-
1985
- 1985-07-18 JP JP15958485A patent/JPS6220580A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5294353A (en) * | 1976-02-04 | 1977-08-08 | Kansai Paint Co Ltd | Production of silica-resin composite |
| JPS60115619A (en) * | 1983-11-28 | 1985-06-22 | Toray Silicone Co Ltd | Thermosetting epoxy resin composition |
| JPS60215087A (en) * | 1984-04-10 | 1985-10-28 | Nissan Motor Co Ltd | Adhesive for fixing vehicle inside mirror |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8536294B2 (en) | 2004-09-02 | 2013-09-17 | The Yokohama Rubber Co., Ltd. | Adhesive composition |
| JP2022538726A (en) * | 2019-05-15 | 2022-09-06 | ダウ グローバル テクノロジーズ エルエルシー | Two-component adhesive composition, article prepared therewith, and method of preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0454713B2 (en) | 1992-09-01 |
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