JPH0454713B2 - - Google Patents
Info
- Publication number
- JPH0454713B2 JPH0454713B2 JP60159584A JP15958485A JPH0454713B2 JP H0454713 B2 JPH0454713 B2 JP H0454713B2 JP 60159584 A JP60159584 A JP 60159584A JP 15958485 A JP15958485 A JP 15958485A JP H0454713 B2 JPH0454713 B2 JP H0454713B2
- Authority
- JP
- Japan
- Prior art keywords
- urethane rubber
- polyamine
- adhesive
- parts
- adhesive 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.)
- Expired - Lifetime
Links
- 239000000853 adhesive Substances 0.000 claims description 27
- 230000001070 adhesive effect Effects 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 12
- 229920006311 Urethane elastomer Polymers 0.000 claims description 11
- 229920000768 polyamine Polymers 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 125000003827 glycol group Chemical group 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 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
- 229910000831 Steel Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-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
- HTSRFYSEWIPFNI-UHFFFAOYSA-N ethyl-dimethoxy-methylsilane Chemical compound CC[Si](C)(OC)OC HTSRFYSEWIPFNI-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 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
- 238000010030 laminating Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- -1 more specifically Substances 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
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000565 sealant 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
- 239000000126 substance Substances 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 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
- Sealing Material Composition (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
【発明の詳細な説明】
産業上の利用分野
本発明はウレタンゴム系接着剤用密着剤組成
物、更に詳しくは、ウレタンゴム系接着剤の密着
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 adhesive compositions for urethane rubber adhesives, more specifically, adhesive compositions added to urethane rubber adhesives in order to improve their adhesion durability. relating to things.
従来技術と解決すべき問題点
通常、接着剤、シーリング材、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、フエノール樹脂、石油樹脂、エポキシ樹脂、
シランカツプリング剤、チタネートカツプリング
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 Normally, adhesives are added to resin compositions such as adhesives, sealants, paints, and injection agents in order to improve their adhesion. Such adhesives include phenolic resin, petroleum resin, epoxy resin,
Silane coupling agents, titanate coupling agents, etc. have been used, but they have not produced satisfactory results in terms of adhesion durability.On the other hand, methods have been taken to increase adhesion by applying a primer to the base. 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
化合物と特定のポリアミンとの反応生成物が、た
とえば塩化ビニルシートと鋼板の接着に多用され
ているウレタンゴム系接着剤に対し所望の密着付
与効果を発揮しうることを見出し、本発明を完成
させるに至つた。 The present inventors conducted intensive research 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 been discovered that a reaction product of an alkoxysilane compound and a specific polyamine can exert a desired adhesion effect on urethane rubber adhesives, which are often used for adhering vinyl chloride sheets and steel plates, for example, and have developed the present invention. I was able to complete it.
発明の構成と効果
すなわち、本発明は、ウレタンゴム系接着剤に
使用する、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密着剤組成物
であつて、上記ポリアミンが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
あり、該密着剤組成物の使用量が固形分換算でウ
レタンゴム系接着剤100重量部に対し、0.1〜20重
量部であることを特徴とするウレタンゴム系接着
剤用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 comprising a reaction product of an epoxyalkylalkoxysilane and a polyamine for use in a urethane rubber adhesive, wherein the polyamine has a propylene glycol skeleton. For use in urethane rubber adhesives, which is an aliphatic polyether polyamine, and the amount of the adhesive composition used is 0.1 to 20 parts by weight per 100 parts by weight of the urethane rubber adhesive in terms of solid content. The present invention provides an adhesive composition.
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−グリシドキシプロ
ジピルメチルエトキシシラン、γ−グリシドキシ
プロピルメチルジエトキシシラン、γ−グリシド
キシプロピルトリメトキシシラン、β−（３，４
−エポキシシクロヘキシル）エチルトリメトキシ
シラン、β−（３，４−エポキシシクロヘキシル）
エチルメチルジメトキシシランなどが挙げられ
る。 Examples of the epoxyalkylalkoxysilane in the present invention include γ-glycidoxyprodipylmethylethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-(3,4
-Epoxycyclohexyl)ethyltrimethoxysilane, β-(3,4-epoxycyclohexyl)
Examples include ethylmethyldimethoxysilane.
本発明で用いるポリアミンは、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。 The polyamine used in the present invention 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℃）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.). At room temperature or under heating (40 to 60℃) in a diluted solution state mixed with ester type)
It may be carried out 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ウレタンゴム系接着剤
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、優れた密着力
（特に水中下の密着耐久性）を付与しうることが
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 it can be used as a urethane rubber adhesive composition in terms of solid content.
Usually 0.1 to 20 parts per 100 parts (parts by weight, same below)
It has been found that excellent adhesion (particularly adhesion durability under water) can be imparted by adding within the range of 50%.
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
エポキシアルキルアルコキシシラン（チツソ社
製、サイラエースＳ−510）24部、脂肪族ポリエ
ーテルポリアミン（三井石油化学エポキシ社、エ
ポミツクＱ−691）６部およびトルエン120部を密
閉容器に入れ、50℃で24時間反応させて（なお、
IRにてエポキシ基および第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。Example 1 24 parts of epoxyalkylalkoxysilane (manufactured by Chitsuso Co., Ltd., Sila Ace S-510), 6 parts of aliphatic polyether polyamine (Mitsui Petrochemical Epoxy Co., Ltd., Epomic Q-691) and 120 parts of toluene were placed in a sealed container, Incubate at ℃ for 24 hours (in addition,
The reaction is terminated by confirming the disappearance of absorption of epoxy groups and secondary amino groups by IR), 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、パンデツクス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シートの積層接着に用いて評価する。
この場合、常態強度は4.5Kg／25mmであつた。Adhesion test Urethane rubber adhesive (Dainippon Ink & Chemicals)
Co., Ltd., Pandex T-5205) was diluted and dissolved in a mixed solvent of toluene/methyl ethyl ketone to a solid content of 15%, and to 100 parts of this, 1 part of the adhesive composition of Example 1 was added in terms of solid content. The product is evaluated by using it for laminating and adhering Zn steel plates and PVC sheets.
In this case, the normal strength was 4.5Kg/25mm.
これに対し、比較例として密着剤を添加しなか
つた場合の常態強度は0.3Kg／25mmであつた。 On the other hand, as a comparative example, the normal strength was 0.3 kg/25 mm when no adhesive was added.
Claims (1)
アルキルアルコキシシランとポリアミンとの反応
生成物から成る密着剤組成物であつて、上記ポリ
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り、該密着剤
組成物の使用量が固形分換算でウレタンゴム系接
着剤100重量部に対し、0.1〜20重量部であること
を特徴とするウレタンゴム系接着剤用密着剤組成
物。1. An adhesive composition comprising a reaction product of an epoxyalkylalkoxysilane and a polyamine for use in a urethane rubber adhesive, wherein the polyamine is an aliphatic polyether polyamine having a polypropylene glycol skeleton; 1. An adhesive composition for a urethane rubber adhesive, characterized in that the amount of the adhesive composition used is 0.1 to 20 parts by weight based on 100 parts by weight of the urethane rubber adhesive in terms of solid content.
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 |
| EP86109821A EP0209851B1 (en) | 1985-07-18 | 1986-07-17 | Bonding agent and resin composition |
| AU60275/86A AU590298B2 (en) | 1985-07-18 | 1986-07-17 | Bonding agent resin composition |
| DE8686109821T DE3683417D1 (en) | 1985-07-18 | 1986-07-17 | ADHESIVES AND RESIN MIXTURE. |
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 JPS6220580A (en) | 1987-01-29 |
| JPH0454713B2 true 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) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3990693B2 (en) | 2004-09-02 | 2007-10-17 | 横浜ゴム株式会社 | Adhesive composition and method for bonding optical fiber and ferrule |
| JP7329623B2 (en) * | 2019-05-15 | 2023-08-18 | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6220580A (en) | 1987-01-29 |
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