JPH01163281A - Hot-melt adhesive composition - Google Patents
Hot-melt adhesive compositionInfo
- Publication number
- JPH01163281A JPH01163281A JP32080587A JP32080587A JPH01163281A JP H01163281 A JPH01163281 A JP H01163281A JP 32080587 A JP32080587 A JP 32080587A JP 32080587 A JP32080587 A JP 32080587A JP H01163281 A JPH01163281 A JP H01163281A
- Authority
- JP
- Japan
- Prior art keywords
- hot melt
- melt adhesive
- parts
- silane coupling
- hot
- 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 24
- 239000004831 Hot glue Substances 0.000 title claims abstract description 20
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 18
- 125000000524 functional group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 13
- 229920005989 resin Polymers 0.000 abstract description 8
- 239000011347 resin Substances 0.000 abstract description 8
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 abstract description 8
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 abstract description 7
- 229910010272 inorganic material Inorganic materials 0.000 abstract description 7
- 239000011147 inorganic material Substances 0.000 abstract description 7
- -1 glycidoxy group Chemical group 0.000 abstract description 5
- 125000003277 amino group Chemical group 0.000 abstract description 3
- 239000000945 filler Substances 0.000 abstract description 3
- 229920001169 thermoplastic Polymers 0.000 abstract description 3
- 150000003377 silicon compounds Chemical class 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 239000011521 glass Substances 0.000 description 16
- 239000012943 hotmelt Substances 0.000 description 15
- 230000001070 adhesive effect Effects 0.000 description 8
- 239000000539 dimer Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 7
- 239000003599 detergent Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920001083 polybutene Polymers 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 229920006271 aliphatic hydrocarbon resin Polymers 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000001993 dienes Chemical class 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
- 125000003700 epoxy group Chemical group 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
■ 技術分野
本発明は、自動車ヘッドランプ、複層ガラス、ソーラー
集熱器の製造あるいは自動車クォーターウィンドの取付
は等において、ガラス同志あるいはガラスと他の素材と
の接着、シールを目的として使用されるホットメルト接
着剤組成物に関し、特に高温（１００〜２００℃）施行
を行っても長期接着力を有する接着剤組成物に関する。[Detailed Description of the Invention] ■ Technical Field The present invention is applicable to the manufacture of automobile headlamps, double glazing, solar collectors, installation of automobile quarter windows, etc., in which glass is bonded to other materials or glass is bonded to other materials. The present invention relates to hot melt adhesive compositions used for sealing purposes, and particularly to adhesive compositions that have long-term adhesive strength even when used at high temperatures (100 to 200°C).
ＩＩ従来技術
ホットメルト接着剤は、室温では固体であるが、加熱す
ると注入または塗布することができるほどに流動性にな
る熱可塑性材料からなる接着剤で、作業性、経済性に優
れている。II. Prior Art Hot melt adhesives are adhesives made of thermoplastic materials that are solid at room temperature but become fluid enough to be injected or coated when heated, and are excellent in workability and economy.
このため、アプリケーターの発展により従来の溶剤型接
着剤に置き換わり、種々の分野で使用されるに至ってい
る。Therefore, with the development of applicators, they have replaced conventional solvent-based adhesives and have come to be used in various fields.
また、接着される被着体も金属、木材、プラスチック、
ガラス等広い範囲に渡っている。In addition, the adherends to be bonded include metal, wood, plastic,
Covers a wide range of glass, etc.
ところがホットメルト接着剤は、金属、ガラス等の無機
材質に対しては初期接着性は満足する接着力が得られる
が、耐水性、耐洗剤液性等の長期耐久性においては界面
剥離を起こし著しく接着力が低下してしまう欠点がある
。However, hot melt adhesives can provide satisfactory initial adhesion to inorganic materials such as metals and glass, but in terms of long-term durability such as water resistance and detergent resistance, interfacial peeling occurs and is severely degraded. It has the disadvantage that adhesive strength decreases.
このため、一般に無機材質特にガラスへの接着性を改良
するためにシランカップリング剤が幅広く利用されてい
るが、ホットメルト接着剤もシランカップリング剤を添
加することにより、ガラス接着性を改良することができ
る。For this reason, silane coupling agents are generally widely used to improve adhesion to inorganic materials, especially glass, but hot melt adhesives can also improve their adhesion to glass by adding silane coupling agents. be able to.
しかしながら、ホットメルト接着剤の作業時に使用され
るコーティングロール等のアプリケーターの温度は１０
０〜２００℃と高温になるため、アプリケーター中で接
着剤が溶融されている間にシランカップリング剤が揮散
しやすく、長時間高温で置かれるとその効果が著しく低
下しガラス接着性を損う欠点がある。However, the temperature of applicators such as coating rolls used when working with hot melt adhesives is 10
Due to the high temperature of 0 to 200℃, the silane coupling agent easily evaporates while the adhesive is melted in the applicator, and if left at high temperatures for a long time, its effectiveness will be significantly reduced and glass adhesion will be impaired. There are drawbacks.
ＩＩＩ 発明の目的
本発明の目的は、アプリケーター中で１００〜２００℃
の高温で長時間加熱溶融された後でも、ガラス、金属等
の無機材質に対し、耐水性、耐洗剤液性等の長期耐久接
着性に優れたホットメルト接着剤組成物を提供しようと
する。III OBJECTS OF THE INVENTION The object of the present invention is to
To provide a hot melt adhesive composition that has excellent long-term adhesive properties such as water resistance and detergent resistance to inorganic materials such as glass and metal even after being heated and melted at high temperatures for a long time.
■ 発明の構成
本発明者等は、異種のシランカップリング剤の有機官能
基同志を反応させ、２量体化したシランカップリング剤
をホットメルト接着剤に添加すると、従来の単量体の添
加に比べて、加熱溶融時のシランカップリング剤の揮散
が少なく、長時間溶融後も耐久接着性が良好であること
を知見し、本発明に至った。■ Structure of the Invention The present inventors have discovered that by reacting the organic functional groups of different types of silane coupling agents and adding the dimerized silane coupling agent to a hot melt adhesive, it is possible to It was discovered that the silane coupling agent volatilizes less when heated and melted, and the durable adhesiveness is good even after melting for a long time, and the present invention was achieved based on this finding.
すなわち、本発明は、ホットメルト接着剤１００重量部
に対し、２種以上のシランカップリング剤の有機官能基
同志を化学反応させて得られる両末端にアルコキシ基を
有する有機ケイ素化合物０．１〜１０重量部を含有する
ホットメルト接着剤組成物を提供する。That is, in the present invention, 0.1 to 0.1 to 100 parts by weight of an organosilicon compound having an alkoxy group at both ends obtained by chemically reacting organic functional groups of two or more silane coupling agents with 100 parts by weight of a hot melt adhesive. A hot melt adhesive composition containing 10 parts by weight is provided.
以下に本発明の構成を、詳細に説明する。The configuration of the present invention will be explained in detail below.
本発明に用いるホットメルト接着剤は、用途に応じてい
かなる組成のものでもよいが、一般に熱可塑性ポリマー
、粘着付与樹脂、ワックス、充填剤、可塑剤、老防剤等
からなる。The hot melt adhesive used in the present invention may have any composition depending on the intended use, but generally comprises a thermoplastic polymer, a tackifying resin, a wax, a filler, a plasticizer, an antiaging agent, and the like.
（１）熱可塑ポリマーは、エチレン−酢酸ビニル共重合
体、エチレン−アクリル酸エステル共重合体、低密度ポ
リエチレン、アタクチックポリプロピレン、スチレン−
ジエン系ブロック共重合体（スチレン−ブタジェン−ス
チレンブロック共重合体、スチレン−イソプレン−スチ
レンブロック共重合体など）、ブチルゴム等を代表的に
挙げることができる。(1) Thermoplastic polymers include ethylene-vinyl acetate copolymer, ethylene-acrylic ester copolymer, low-density polyethylene, atactic polypropylene, and styrene-vinyl acetate copolymer.
Typical examples include diene block copolymers (styrene-butadiene-styrene block copolymers, styrene-isoprene-styrene block copolymers, etc.), butyl rubber, and the like.
（２）粘着付与樹脂としては、天然ロジン、ロジン変性
体、テルペン樹脂、テルペンフェノール樹脂、アルキル
フェノール樹脂、石油樹脂、クマロン−インデン樹脂等
が代表的に挙げられ、これらの１種または２種以上が混
合して使用される。(2) Typical tackifying resins include natural rosin, modified rosin, terpene resin, terpene phenol resin, alkylphenol resin, petroleum resin, coumaron-indene resin, etc. One or more of these resins may be used. used in combination.
（３）ワックス類としてはパラフィンワックス、マイク
ロパラフィンワックス、低分子量ポリエチレン、フィッ
シャートロプシュワックス等の１種または２ ｆｆｆｉ
以上の混合物が使用される。(3) One or two waxes such as paraffin wax, microparaffin wax, low molecular weight polyethylene, Fischer-Tropsch wax, etc.
Mixtures of the above are used.
（４）ホットメルト接着剤には、その他、必要に応じて
公知の可塑剤、充填剤、酸化防止剤等を使用することが
できる。(4) In addition, known plasticizers, fillers, antioxidants, etc. can be used in the hot melt adhesive, if necessary.
本発明は、両末端にアルコキシ基を有する有機ケイ素化
合物を含有することに特徴がある。The present invention is characterized by containing an organosilicon compound having alkoxy groups at both ends.
シランカップリング剤は、Ｓｔ （ＯＲ）３部と、ビニ
ル基、アミノ基、エポキシ基などの有機官能基部分から
なる。 本発明では、異なる有機官能基部分を有する異
種のシランカップリング剤を２種以上あらかじめ有機官
能基部分で反応させて２量体化する。The silane coupling agent consists of 3 parts of St (OR) and an organic functional group moiety such as a vinyl group, an amino group, or an epoxy group. In the present invention, two or more different types of silane coupling agents having different organic functional group moieties are reacted in advance at the organic functional group moieties to form a dimer.
シランカップリング剤としては、
γ−アミノプロピルトリエトキシシラン、Ｎ−β−（ア
ミノエチル）−γ−アミノプロピルトリメトキシシラン
、Ｎ−β−（アミノエチル）−γ−アミノプロピルメチ
ルジメトキシシラン、γ−グリシドオキシプロビルトリ
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、γ−グリシドキシプロピ
ルメチルヂエトキシシラン、γ−メルカプトプロピルト
リメトキシシラン、ビニルトリエトキシシラン、ビニル
トリメトキシシラン等を代表的に挙げることができ、こ
れらのシランカップリング剤の有機官能基同志を反応さ
せて２量体以上とする。As the silane coupling agent, γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, N-β-(aminoethyl)-γ-aminopropylmethyldimethoxysilane, γ -glycidoxypropyltrimethoxysilane, β-(3,4-epoxycyclohexylethyltrimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, γ-mercaptopropyltrimethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane) Methoxysilane and the like are representative examples, and the organic functional groups of these silane coupling agents are reacted with each other to form a dimer or more.
反応させる有機官能基部分の組合せは、グリシドオキシ
基とアミノ基あるいはメルカプト基、ビニル基とメルカ
プト基、が好ましい。The combination of organic functional groups to be reacted is preferably a glycidoxy group and an amino group or a mercapto group, or a vinyl group and a mercapto group.
例えば、γ−グリシドオキシプロビルトリメトキシシラ
ンとγ−アミノプロピルトリエトキシシランあるいはγ
−メルカプトプロピルトリメトキシシランとの反応物、
ビニルトリメトキシシランとγ−メルカプトプロピルト
リメトキシシランとの反応物等が有効である。For example, γ-glycidoxypropyltrimethoxysilane and γ-aminopropyltriethoxysilane or γ
- reaction product with mercaptopropyltrimethoxysilane,
A reaction product of vinyltrimethoxysilane and γ-mercaptopropyltrimethoxysilane is effective.
これらの２量体以上の有機ケイ素化合物は、１種類でも
よいし２種以上の混合物であってもよい。These dimer or more organosilicon compounds may be one type or a mixture of two or more types.
シランカップリング剤は、２量体以上の多量体化するこ
とにより、アプリケーターで長時間加熱溶融されても、
ホットメルト接着剤組成物からの揮散が少なく、ガラス
、金属等の無機材質に対し長期耐久接着性が維持できる
。By converting the silane coupling agent into a dimer or higher polymer, even if it is heated and melted with an applicator for a long time,
There is little volatilization from the hot melt adhesive composition, and long-term durable adhesiveness can be maintained on inorganic materials such as glass and metal.
異種のシランカップリング剤を２Ｒ体化する方法はいか
なる方法でもよいが、はぼ等モルの２種のシランカップ
リング剤同志を混合し、８０〜１００℃で１５時間反応
させる。Any method may be used to convert different types of silane coupling agents into 2R forms, but approximately equimolar amounts of two types of silane coupling agents are mixed together and reacted at 80 to 100°C for 15 hours.
また、必要により、３級アミン、錫系有機金属等の触媒
を添加して反応させる。Further, if necessary, a catalyst such as a tertiary amine or a tin-based organic metal is added to cause the reaction.
上述の有機ケイ素化合物は、ホットメルト接着剤１００
重量部に対して、０．１〜１０部を添加する。 ０．１
重量部未満では接着性の向上効果が見られず、１０重量
部超添加しても、０．１〜１０部添加した場合に比べて
効果は変らず経済的に利点がない。The above-mentioned organosilicon compound is used in hot melt adhesive 100
Add 0.1 to 10 parts based on weight part. 0.1
If it is less than 1 part by weight, no effect of improving adhesion is observed, and even if it is added in excess of 10 parts by weight, the effect will not change compared to the case where 0.1 to 10 parts are added, and there will be no economic advantage.
■ 実施例 以下に実施例により更に具体的に説明する。■ Example This will be explained in more detail below using Examples.
（実施例１〜３）
γ−グリシドオキシプロビルトリメトキシシラン（日本
ユニカー、シリコンＡ−１８７）１００部に対し、γ−
アミノプロピルトリエトキシシラン（日本ユニカー、シ
リコンＡ１１００）９４部を８０℃にて１５時間反応さ
せ、２量体の有機ケイ素化合物を得た。 エチレン−酢
酸ビニル共重合体（三井石油化学、エバフレックス＃２
２０、ＶＡ含有量２８重量％）４０部、ロジン誘導体（
荒用化学、ペンセルＡ）４０部、１４５”Ｆパラフィン
ワックス（日木精蝋、５Ｐ４５）１５部、可塑剤ＤＯＰ
５部を２００℃にて加熱溶融してホットメルト基材とし
、上記２量体の有機ケイ素化合物をそれぞれ０．１．５
．１０部添加してホットメルト組成物を作った。(Examples 1 to 3) γ-
94 parts of aminopropyltriethoxysilane (Nippon Unicar, Silicone A1100) was reacted at 80° C. for 15 hours to obtain a dimeric organosilicon compound. Ethylene-vinyl acetate copolymer (Mitsui Petrochemical, Evaflex #2
20, VA content 28% by weight) 40 parts, rosin derivative (
Arayo Kagaku, Pencell A) 40 parts, 145"F paraffin wax (Hiki Seiro, 5P45) 15 parts, plasticizer DOP
5 parts were heated and melted at 200°C to form a hot melt base material, and 0.1.5 parts of each of the above dimer organosilicon compounds were melted at 200°C.
．． A hot melt composition was prepared by adding 10 parts.
（比較例１〜２）
実施例１〜３と同様にして、ただし同様の２量体の有機
ケイ素化合物をそれぞれ０．０５．１５部添加してホッ
トメルト組成物を得た。(Comparative Examples 1 to 2) Hot melt compositions were obtained in the same manner as in Examples 1 to 3, except that 0.05.15 parts of the same dimeric organosilicon compounds were added to each.
（比較例３）
実施例１〜３と同様にして、ただし実施例で用いた２量
体の有機ケイ素化合物は使用せず、その代りにγ−グリ
シドオキシプロピルトリメトキシシランを１０部添加し
てホットメルト組成物を得た。(Comparative Example 3) In the same manner as Examples 1 to 3, except that the dimer organosilicon compound used in the example was not used, and instead, 10 parts of γ-glycidoxypropyltrimethoxysilane was added. A hot melt composition was obtained.
（実施例４〜６）
実施例１〜３と同様のホットメルト基材を調製し加熱溶
融後、γ−グリシドオキシプロピルトリメトキシシラン
１００部に対しγ−メルカプトプロピルトリメトキシシ
ラン（日本ユニカー、シリコンＡ１８９）８３部を３級
アミン等の触媒により反応させた化合物をそれぞれ０．
１．５．１０部添加しホットメルト組成物を得た。(Examples 4 to 6) Hot melt base materials similar to those in Examples 1 to 3 were prepared, and after heating and melting, γ-mercaptopropyltrimethoxysilane (Nippon Unicar Co., Ltd.) was added to 100 parts of γ-glycidoxypropyltrimethoxysilane. A compound prepared by reacting 83 parts of silicon A189) with a catalyst such as a tertiary amine was mixed with 0.
1.5.10 parts were added to obtain a hot melt composition.
（比較例４〜５）
実施例４〜６と同様に、ただし反応化合物をそれぞれ０
．０５．１５部添加してホットメルト組成物を得た。(Comparative Examples 4 to 5) Same as Examples 4 to 6, except that 0 of each of the reaction compounds was used.
．． A hot melt composition was obtained by adding 05.15 parts.
（実施例７〜９）
γ−グリシドオキシプロビルトリメトキシシラン（日本
ユニカー、シリコンＡ１８７）１００部に対し、γ−ア
ミノプロピルトリエトキシシラン（日本ユニカー、シリ
コンＡ１１００）９４部を８０℃にて１５時間反応させ
、２量体の有機ケイ素化合物を得た。 ブチルゴム（ポ
リサー、ブチルＰＢ−４０２）１０部、脂肪族系炭化水
素樹脂（エクソン化学、エスコレッツ１３１０）７部、
液状ポリブテン（日本石油化学、ポリブテンＨＶ−１０
０）３７部、タルフ（富士タルフＴ−９９）４６部を２
００℃にて加熱溶融し、上記２量体の有機ケイ素化合物
をそれぞれ０．１．５．１０１添加してホットメルト組
成物を作った。(Examples 7 to 9) 94 parts of γ-aminopropyltriethoxysilane (Nippon Unicar, Silicone A1100) was added to 100 parts of γ-glycidoxypropyltrimethoxysilane (Nippon Unicar, Silicone A187) at 80°C. The reaction was continued for 15 hours to obtain a dimeric organosilicon compound. 10 parts of butyl rubber (Polycer, Butyl PB-402), 7 parts of aliphatic hydrocarbon resin (Exxon Chemical, Escolets 1310),
Liquid polybutene (Japan Petrochemical, Polybutene HV-10
0) 37 parts, 46 parts of Tarf (Fuji Tarf T-99) 2
The mixture was heated and melted at 00° C., and 0.1.5.101 of each of the dimer organosilicon compounds described above were added to prepare a hot melt composition.
（比較例６〜７）
実施例７〜９と同様にして、ただし同様の２量体の有機
ケイ素化合物をそれぞれ０．０５．１５部添加してホッ
トメルト組成物を得た。(Comparative Examples 6 to 7) Hot melt compositions were obtained in the same manner as in Examples 7 to 9, except that 0.05.15 parts of the same dimeric organosilicon compounds were each added.
（比較例８）
実施例７〜９と同様にして、ただし実施例で用いた２量
体の有機ケイ素化合物は使用せず、その代りにγ−グリ
シドオキシプロピルトリメトキシシランを１０部添加し
てホットメルト組成物を得た。(Comparative Example 8) In the same manner as Examples 7 to 9, except that the dimer organosilicon compound used in the example was not used, and instead, 10 parts of γ-glycidoxypropyltrimethoxysilane was added. A hot melt composition was obtained.
以上の実施例１〜９、比較例１〜８を用いて２０℃にお
ける剥離試験を行い、ガラス接着性を評価した。Using the above Examples 1 to 9 and Comparative Examples 1 to 8, a peel test was conducted at 20°C to evaluate glass adhesion.
結果を表Ｉに示す。The results are shown in Table I.
（１）試験片の調整
■ブランクホットメルト
ホットメルト接着剤組成物をアプリケーターにより１９
０〜２００℃に加熱溶融して、長さ２２０ ｍｍ、幅２
５ｍｍの綿布（ＪＩＳＳ号綿布）の一方の端に長さ１０
０ｍｍに塗布し、３０秒後に長さ１２０ ｍｍ、幅２５
ｍｍ、厚み５ｍｍのガラスを圧着し、メルト厚さを２ｍ
ｍになるように圧着する。 １〜２時間放置後、はみ
出した部分を切断して試験片とし、２０℃恒温室にて２
４時間放置後のものをブランクホットメルト試験片とし
た。(1) Preparation of test piece■ Apply the blank hot melt hot melt adhesive composition using an applicator for 19 minutes.
Heat and melt at 0 to 200℃, length 220 mm, width 2
A length of 10 mm is attached to one end of a 5 mm cotton cloth (JISS cotton cloth).
0mm, and after 30 seconds the length is 120mm and the width is 25mm.
mm, 5mm thick glass is crimped and the melt thickness is 2m.
Crimp it so that it becomes m. After leaving it for 1 to 2 hours, cut the protruding part to make a test piece, and store it in a constant temperature room at 20℃ for 2 hours.
The blank hot melt test piece was prepared after being left for 4 hours.
■熱老化ホットメルト
熱老化ホットメルトは、ホットメルト接着剤組成物をノ
ードソン社製アプリケーター１８型に５ｋｇ投入し、２
００℃にて４８時間加熱溶融させたものを使用し、ブラ
ンクホットメルトの場合と同様にして試験片を作製した
。■Heat-aged hot melt Heat-aged hot melt is made by putting 5 kg of the hot melt adhesive composition into Nordson applicator model 18,
A test piece was prepared in the same manner as in the case of the blank hot melt using a material heated and melted at 00° C. for 48 hours.
（２）耐水性試験
耐水性は試験片を４０℃の温水へ４週間浸漬し、２０℃
にて１時間放置してから剥離試験に供した。(2) Water resistance test Water resistance was determined by immersing the test piece in warm water at 40°C for 4 weeks.
After leaving it for 1 hour, it was subjected to a peel test.
（３）耐洗剤液性試験
耐洗剤液性は試験片を液体洗剤トップ（ライオン（株）
製）の１０％水溶液に２０℃にて４週間浸漬した後水洗
いをして２０℃にて１時間放置し剥離試験に供した。(3) Detergent liquid resistance test For detergent liquid resistance test, the test piece was prepared using liquid detergent top (Lion Co., Ltd.)
After 4 weeks of immersion in a 10% aqueous solution of 2000 (manufactured by M. Co., Ltd.) at 20°C, the sample was washed with water, left at 20°C for 1 hour, and subjected to a peel test.
（４）剥離試験
試験片に約１０ｍｍごとにカッターナイフによりガラス
面に達するカットを入れて、２０℃で、速度２００ ｍ
ｍ７分にて引張試験を行った。(4) Peeling test The test piece was cut with a cutter knife every 10 mm to reach the glass surface, and the test piece was heated at 20°C and at a speed of 200 m.
A tensile test was conducted for 7 minutes.
ガラス接着性の評価は以下のように行った。Glass adhesion was evaluated as follows.
◎ガラス界面剥離なし
△ガラス界面剥離面積５〜３０％
×ガラス界面剥離面積３０％超
■ 発明の効果
本発明の接着剤組成物は、異種のシランカップリング剤
の反応物を含有するので、耐水性耐洗剤液性を指標とす
る無機材質との接着性が良い。◎No peeling at the glass interface △Glass interface peeling area 5-30% ×Glass interface peeling area over 30%■ Effects of the invention The adhesive composition of the present invention contains reactants of different types of silane coupling agents, so it is water resistant. Good adhesion to inorganic materials as measured by detergent resistance.
しかも、施行時に高温（２００℃）で長時間（４８時間
）溶融しても耐水性耐洗剤液性等の無機材質との接着性
が優れている。Moreover, even when melted at high temperature (200° C.) for a long time (48 hours) during application, it has excellent adhesion to inorganic materials such as water resistance and detergent resistance.
Claims (1)
上のシランカップリング剤の有機官能基同志を化学反応
させて得られる両末端にアルコキシ基を有する有機ケイ
素化合物０．１〜１０重量部を含有することを特徴とす
るホットメルト接着剤組成物。(1) 0.1 to 10 parts by weight of an organosilicon compound having alkoxy groups at both ends obtained by chemically reacting the organic functional groups of two or more silane coupling agents to 100 parts by weight of the hot melt adhesive. A hot melt adhesive composition comprising:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32080587A JP2650696B2 (en) | 1987-12-18 | 1987-12-18 | Hot melt adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32080587A JP2650696B2 (en) | 1987-12-18 | 1987-12-18 | Hot melt adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01163281A true JPH01163281A (en) | 1989-06-27 |
| JP2650696B2 JP2650696B2 (en) | 1997-09-03 |
Family
ID=18125434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32080587A Expired - Lifetime JP2650696B2 (en) | 1987-12-18 | 1987-12-18 | Hot melt adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2650696B2 (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0434269A2 (en) * | 1989-12-11 | 1991-06-26 | Bridgestone Corporation | Sandwich glass |
| EP0540040A1 (en) * | 1991-10-31 | 1993-05-05 | Dow Corning Toray Silicone Company, Limited | Room-temperature-curable organopolysiloxane composition |
| KR100546453B1 (en) * | 1997-08-28 | 2006-04-20 | 린텍 가부시키가이샤 | Pressure sensitive adhesive sheet using pressure sensitive adhesive composition and pressure sensitive adhesive prepared from this composition |
| US8101276B2 (en) | 2008-09-16 | 2012-01-24 | Henkel Corporation | Pressure sensitive adhesive compositions and articles prepared using such compositions |
| US8440304B2 (en) | 2008-09-16 | 2013-05-14 | Henkel Corporation | Acrylic pressure sensitive adhesive formulation and articles comprising same |
| US9365751B2 (en) | 2012-07-24 | 2016-06-14 | Henkel IP & Holding GmbH | Reactive hot melt adhesive |
| US9428677B2 (en) | 2013-01-24 | 2016-08-30 | Henkel IP & Holding GmbH | Reactive hot melt adhesive |
| US10221346B2 (en) | 2014-01-14 | 2019-03-05 | Henkel IP & Holding GmbH | Reactive hot melt adhesives with improved adhesion |
| JPWO2018074070A1 (en) * | 2016-10-18 | 2019-04-25 | 株式会社Moresco | Hot melt adhesive |
-
1987
- 1987-12-18 JP JP32080587A patent/JP2650696B2/en not_active Expired - Lifetime
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0434269A2 (en) * | 1989-12-11 | 1991-06-26 | Bridgestone Corporation | Sandwich glass |
| EP0540040A1 (en) * | 1991-10-31 | 1993-05-05 | Dow Corning Toray Silicone Company, Limited | Room-temperature-curable organopolysiloxane composition |
| KR100546453B1 (en) * | 1997-08-28 | 2006-04-20 | 린텍 가부시키가이샤 | Pressure sensitive adhesive sheet using pressure sensitive adhesive composition and pressure sensitive adhesive prepared from this composition |
| US8101276B2 (en) | 2008-09-16 | 2012-01-24 | Henkel Corporation | Pressure sensitive adhesive compositions and articles prepared using such compositions |
| US8440304B2 (en) | 2008-09-16 | 2013-05-14 | Henkel Corporation | Acrylic pressure sensitive adhesive formulation and articles comprising same |
| US9365751B2 (en) | 2012-07-24 | 2016-06-14 | Henkel IP & Holding GmbH | Reactive hot melt adhesive |
| US9428677B2 (en) | 2013-01-24 | 2016-08-30 | Henkel IP & Holding GmbH | Reactive hot melt adhesive |
| US10221346B2 (en) | 2014-01-14 | 2019-03-05 | Henkel IP & Holding GmbH | Reactive hot melt adhesives with improved adhesion |
| JPWO2018074070A1 (en) * | 2016-10-18 | 2019-04-25 | 株式会社Moresco | Hot melt adhesive |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2650696B2 (en) | 1997-09-03 |
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