JPS62290736A - Heat-resistant silane coupling agent - Google Patents
Heat-resistant silane coupling agentInfo
- Publication number
- JPS62290736A JPS62290736A JP13344986A JP13344986A JPS62290736A JP S62290736 A JPS62290736 A JP S62290736A JP 13344986 A JP13344986 A JP 13344986A JP 13344986 A JP13344986 A JP 13344986A JP S62290736 A JPS62290736 A JP S62290736A
- Authority
- JP
- Japan
- Prior art keywords
- coupling agent
- silane coupling
- bis
- heat
- molecule
- 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
- 239000006087 Silane Coupling Agent Substances 0.000 title claims abstract description 24
- -1 aromatic amino silane compound Chemical class 0.000 claims abstract description 16
- 125000005369 trialkoxysilyl group Chemical group 0.000 claims abstract description 7
- 229910000077 silane Inorganic materials 0.000 claims description 7
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 230000008878 coupling Effects 0.000 abstract description 5
- 238000010168 coupling process Methods 0.000 abstract description 5
- 238000005859 coupling reaction Methods 0.000 abstract description 5
- 238000009835 boiling Methods 0.000 abstract description 4
- 238000001704 evaporation Methods 0.000 abstract description 4
- 230000008020 evaporation Effects 0.000 abstract description 3
- 238000000859 sublimation Methods 0.000 abstract description 3
- 230000008022 sublimation Effects 0.000 abstract description 3
- LXJLFVRAWOOQDR-UHFFFAOYSA-N 3-(3-aminophenoxy)aniline Chemical compound NC1=CC=CC(OC=2C=C(N)C=CC=2)=C1 LXJLFVRAWOOQDR-UHFFFAOYSA-N 0.000 abstract description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 150000004984 aromatic diamines Chemical class 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 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 2
- 239000004593 Epoxy Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 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
- 150000001875 compounds Chemical class 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 2
- FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- JEZFASCUIZYYEV-UHFFFAOYSA-N chloro(triethoxy)silane Chemical compound CCO[Si](Cl)(OCC)OCC JEZFASCUIZYYEV-UHFFFAOYSA-N 0.000 description 1
- CBVJWBYNOWIOFJ-UHFFFAOYSA-N chloro(trimethoxy)silane Chemical compound CO[Si](Cl)(OC)OC CBVJWBYNOWIOFJ-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 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
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- SNZXFRFQGXSSGN-UHFFFAOYSA-N phenylsulfanyloxysulfanylbenzene Chemical compound C=1C=CC=CC=1SOSC1=CC=CC=C1 SNZXFRFQGXSSGN-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Abstract
Description
【発明の詳細な説明】
３、発明の詳細な説明
（ａ）産業上の利用分野
本発明は、加熱時の昇華や蒸発が防止された耐熱性シラ
ンカップリング剤に関するものである。Detailed Description of the Invention 3. Detailed Description of the Invention (a) Field of Industrial Application The present invention relates to a heat-resistant silane coupling agent that is prevented from sublimating or evaporating during heating.
（ｂ）従来の技術
シランカップリング剤は一磯物と有機物との界面の接着
を確実に行わせる手段として叫１広く使用されている。(b) Prior Art Silane coupling agents are widely used as a means for ensuring the adhesion of the interface between a rock material and an organic material.
シランカップリング剤を、エポキシ樹脂、不飽和ポリエ
ステル樹脂、７エ／−ル４４（１ｉＴ］、ポリサルファ
イド、ポリアミドなどの熱硬化性ＦＭ脂や熱可塑性樹脂
に０．１〜１重量％添加すると、金属やガラスへの接着
性が改善される。When 0.1 to 1% by weight of a silane coupling agent is added to a thermosetting FM resin or thermoplastic resin such as epoxy resin, unsaturated polyester resin, 7E/-L44 (1iT), polysulfide, or polyamide, metal Improved adhesion to glass.
またシランカップリング剤を適当な濃度の溶液とし、あ
らかじめプライマーとして塗布すると、接着性が改善さ
れる。Furthermore, adhesion can be improved by preparing a solution of a silane coupling agent at an appropriate concentration and applying it as a primer in advance.
実用的には、上記の熱硬化性用脂もしくは熱可塑性樹脂
である有機物にガラスや金属等の無機物を配合すると、
接着性が改善されるから接着増強剤（充填剤）として用
いられる。Practically speaking, when an inorganic substance such as glass or metal is blended with an organic substance such as the above-mentioned thermosetting fat or thermoplastic resin,
It is used as an adhesion enhancer (filler) because it improves adhesion.
これらのシランカップリング剤は、分子中のシラン側の
末端がガラスなど無機物に配向してくっつき、一方、ア
ミ７基などの有機基がエポキシなど有機物に配向してく
っつき、この両者の作用によって接着性が改善される。In these silane coupling agents, the silane side end of the molecule is oriented and sticks to an inorganic substance such as glass, while the organic group such as amine 7 group is oriented to and sticks to an organic substance such as epoxy, and the action of these two forms an adhesive. sex is improved.
従来、かかるシランカップリング剤としては、ビニルト
リエトキシシラン、ビニル−トリス（β−メトキシエト
キシ）−シラン、ビニルトリアセトキシシラン等のビニ
ル系ンラン化合物、γ−アミノプロピルトリエトキシシ
ラン、γ−タロロプロビルトリメトキシシラン、γ−（
β−アミ／エチル）アミノプロピルトリメトキシシラン
、γ−メタクリロ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）二チルトリメト
キシシラン、γ−グリシドキシプロビルトリノトキシシ
ラン、γ−メルカプトプロピルトリメトキシシラン、γ
−（アミノエチル）−γ−７ミ／プロピルトリエトキシ
シラン等のトリアルコキシシラン化合物が用いられてい
た。Conventionally, such silane coupling agents include vinyl triethoxysilane, vinyl-tris(β-methoxyethoxy)-silane, vinyltriacetoxysilane, and other vinyl-based silane compounds, γ-aminopropyltriethoxysilane, γ-talolopropylene, etc. Viltrimethoxysilane, γ-(
β-amino/ethyl)aminopropyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane, β
-(3,4-epoxycyclohexyl)dityltrimethoxysilane, γ-glycidoxyprobyltrinotoxysilane, γ-mercaptopropyltrimethoxysilane, γ
Trialkoxysilane compounds such as -(aminoethyl)-γ-7mi/propyltriethoxysilane have been used.
（ｃ）発明が解決しようとする問題点
しかしながら、従来のトリエトキシシラン化合物（シラ
ンカップリング剤）を添加して成る樹脂組成物を、加熱
して成形、注形、塗装等の加工処理する際に、このトリ
エトキシシラン化合物（シランカップリング剤）が昇華
や蒸発し、これによって気泡が発生したり、本来のカッ
プリング機能が低下したりするなどの傾向があった。(c) Problems to be solved by the invention However, when processing a resin composition made by adding a conventional triethoxysilane compound (silane coupling agent) by heating, molding, casting, painting, etc. Moreover, this triethoxysilane compound (silane coupling agent) tends to sublimate or evaporate, which tends to generate bubbles and reduce the original coupling function.
特に、熱硬化性樹脂を用い、これを溶融塗装する場合に
おいては、このとき塗膜中において顕著に気泡が発現し
、絶縁性や防食性に悪影響を及ぼすなどの問題があった
。In particular, when a thermosetting resin is used and melt-painted, there is a problem that air bubbles are noticeably generated in the coating film, which adversely affects insulation and anticorrosion properties.
（ｄ）問題点を解決するための手段
本発明者らは、上記問題点を解決すべり、゛鋭意検討を
重ねた結果、加熱処理しても昇華や蒸発がおこりにくく
、しかも、優れたカップリング機能を有する耐熱性シラ
ンカップリング剤を見い出し、本発明を完成するに至っ
たものである。(d) Means for Solving the Problems The inventors of the present invention have solved the above-mentioned problems and have found that, as a result of extensive studies, they have achieved an excellent coupling that is resistant to sublimation or evaporation even after heat treatment. The inventors discovered a functional heat-resistant silane coupling agent and completed the present invention.
即ち、本発明は、分子内にトリアルコキシシリル基を２
つ以上含む芳香族アミン系のシラン化合物から成る耐熱
性シランカップリング剤を特徴とするものでである。That is, the present invention has two trialkoxysilyl groups in the molecule.
The present invention is characterized by a heat-resistant silane coupling agent comprising an aromatic amine-based silane compound containing at least one aromatic amine-based silane compound.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明に用いられる、分子内にトリアルコキシシリル基
を２つ以上含む芳香族アミン系のシラン化合物としては
、特に限定されるものではなく、具体的な代表例として
は、Ｎ、Ｎ’−ビス （トリメトキシシリル）ノアミノ
ジフェニルメタン、Ｎ。The aromatic amine-based silane compound containing two or more trialkoxysilyl groups in the molecule used in the present invention is not particularly limited, and typical examples include N,N'-bis (trimethoxysilyl)noaminodiphenylmethane, N.
Ｎ゛−ビス（トリエトキシシリル）ノアミノジフェニル
メタン、Ｎ、Ｎ’−ビス（トリメトキシシリル）ジアミ
ノジフェニルエーテル、Ｎ、Ｎ’−ビス （トリメトキ
シシリル）ジアミノジフェニルスルホン、Ｎ、Ｎ’−ビ
ス（トリットキンシリル）ノアミノジフェニルチオエー
テル、Ｎ、Ｎ’−ビス（トリエトキシシリル）ノアミノ
ジフェニルエーテル、Ｎ、Ｎ’−ビス（トリエトキシシ
リル）ノアミノジフェニルスルホン、Ｎ、Ｎ’−ビス（
トリエトキシシリル）ノアミノジフェニルチオエーテル
、Ｎ−）リエトキシーＮ ’−トリノトキシジアミ７ジ
フェニルメタン、Ｎ、Ｎ’−ビス（トリプロポキン）ノ
アミノジフェニルメタン等が挙げられる。N゛-bis(triethoxysilyl)noaminodiphenylmethane, N,N'-bis(trimethoxysilyl)diaminodiphenyl ether, N,N'-bis(trimethoxysilyl)diaminodiphenyl sulfone, N,N'-bis(trit) quinsilyl) noaminodiphenyl thioether, N,N'-bis(triethoxysilyl)noaminodiphenyl ether, N,N'-bis(triethoxysilyl)noaminodiphenyl sulfone, N,N'-bis(
Examples include triethoxysilyl)noaminodiphenylthioether, N-)liethoxyN'-trinotoxydiami7diphenylmethane, N,N'-bis(tripropoquine)noaminodiphenylmethane, and the like.
上記シラン化合物は芳香族ノアミツ１モルに対しトリア
ルコキシシリルクロライドを２〜３モルの割合で常法に
従い反応させて得ることができる。The above-mentioned silane compound can be obtained by reacting trialkoxysilyl chloride in a proportion of 2 to 3 moles per mole of aromatic nitrate according to a conventional method.
上記芳香族ノアミノ化合物としては、特に限定されるも
のではないが、常圧での沸点が３００ ’Ｃ以上のもの
が最も好ましい。The aromatic noamino compound is not particularly limited, but those having a boiling point of 300'C or higher at normal pressure are most preferred.
その具体的な代表例としては、３，３゛−ジアミノジフ
ェニルエーテル、４，４”−ノアミノジフェニルメタン
、３．３’−ノアミノジフェニルメタン、ジアミノベン
ゾフェノン、４，４゛−ノアミ／ノフェニルプロパン、
ベンツジン、３．３’−ジメチルベンツノン、３，３゛
−ノメトキシー＝８ 、．４ ’−ノアミノノフェニル
メタン、３，３′−ツメチル−４、４’−ノアミノノフ
ェニルメタン、４．４’−ジアミノジフェニルスルホン
、ノアミノジフェニルチオエーテル、４，４°−シー（
３−７ミノ７エ／キシ）ジフェニルスルホン、４，４゛
−ジー（３−アミノフェノキシ）ジフェニルプロパン、
４．４’−ジアミノジフェニルエーテル３，４′−ノア
ミノジフェニルエーテル、 ２，２−ビス（４−７ミ／
フエニル）プロパン、 １，３−ビス（アミ／フェノキ
シ）ベンゼン等が挙げられる。Specific representative examples include 3,3'-diaminodiphenyl ether, 4,4''-noaminodiphenylmethane, 3,3'-noaminodiphenylmethane, diaminobenzophenone, 4,4''-noami/nophenylpropane,
Benzuzine, 3,3'-dimethylbenzenone, 3,3'-nomethoxy=8,. 4'-Noaminophenylmethane, 3,3'-tumethyl-4,4'-noaminophenylmethane, 4,4'-diaminodiphenylsulfone, noaminodiphenylthioether, 4,4°-cy(
3-7mino7eth/xy)diphenylsulfone, 4,4゛-di(3-aminophenoxy)diphenylpropane,
4.4'-Diaminodiphenyl ether 3,4'-Noaminodiphenyl ether, 2,2-bis(4-7mi/
phenyl)propane, 1,3-bis(ami/phenoxy)benzene, and the like.
又、上記トリアルコキシシリルクロライドとしては、例
えばトリメトキシシリルクロライド、トリエトキシシリ
ルクロライド、トリプロポキンシリルクロライド等が挙
げられ、これらは、所望により混合して使用しても差し
つがえない。Further, examples of the above-mentioned trialkoxysilyl chloride include trimethoxysilyl chloride, triethoxysilyl chloride, tripropoquine silyl chloride, etc., and these may be used in combination as desired.
そして、本発明の耐熱性シランカップリング剤は、Ｆ
ＲＰ ”？ Ｆ ＲＴ Ｐ用のガラス繊維のほか、各種
の充填剤の処理、合成樹脂、接着剤、シーラント、コー
キング剤、塗料などへの混合、下地のブライマー処理な
どの素材に広く用いられるが、その配合量は、その目的
や用途、更に上記素材によりても異なるが、一般に、上
記素材１００重量部に対して０．２〜５重量部とするの
が好ましい。The heat-resistant silane coupling agent of the present invention is F
In addition to glass fiber for RP ”? The blending amount varies depending on the purpose, use, and the above-mentioned material, but it is generally preferably 0.2 to 5 parts by weight per 100 parts by weight of the above-mentioned material.
（ｅ）作用
本発明のシランカップリング剤は、芳香族ノアミン骨格
にトリアルコキシシリル基を２つ以上結合した構造を有
しており、沸点が高く、昇華や蒸発が生じにくいから成
形、注形、塗装等の加熱加工処理後の樹脂組成物中に気
泡が生じてカップリング機能を低下させたり、絶縁性や
防食性が低下するのを極力抑える作用を有するのである
。(e) Effect The silane coupling agent of the present invention has a structure in which two or more trialkoxysilyl groups are bonded to an aromatic noamine skeleton, and has a high boiling point and is difficult to sublimate or evaporate, so it can be molded and cast. It has the effect of suppressing as much as possible the formation of air bubbles in the resin composition after heat processing such as painting, which reduces the coupling function and the insulation and anticorrosion properties.
又、本発明のカップリング剤は、分子中において、シラ
ン基側の末端が金属やガラス等の無代物に配向して結合
し、一方、アミ７基などの有機基がエポキシなどの有機
物に配向して結合し、これらによって、優れた接着増強
作用を有するのである。In addition, in the coupling agent of the present invention, in the molecule, the terminal on the silane group side is oriented and bonded to an inorganic substance such as a metal or glass, while the organic group such as an amine 7 group is oriented and bonded to an organic substance such as an epoxy group. These bond together and have an excellent adhesion-enhancing effect.
（ｒ）実施例
以下、本発明を実施例に基づき詳細に説明するが、本発
明はこれに限定されるものではない。(r) Examples Hereinafter, the present invention will be explained in detail based on Examples, but the present invention is not limited thereto.
実、１例１
エポキシ当量７５０のビスフェノールＡ型エポキシ樹脂
１００重量部と、水酸基当量２５０のビスフェノールＡ
とエピクロルヒドリンとから誘導される７エ／−ル樹脂
３３重量部、２−メチルイミダゾール０．８重−ｆｌｉ
Ｌｆｆｌｓ、ルチル型酸化チタン３０重量部、平均粒径
５０μｍのガラスフレーク３０ 重Ｎ ｔａ、２−エチ
ルへキシルアクリレートのオリゴマーからなるアクリル
系流れ調整剤１重１部、シランカップリング剤としてＮ
、 Ｎ ｌ−ビス（トリエトキシシリル）ジアミノノ
フェニルメタン１重量部を各々加えて高速撹拌機で予備
混合後、押出し機で溶融混練した後冷却し、粉砕して平
均粒径６０μｍの粉体塗料を得た。Actually, Example 1: 100 parts by weight of bisphenol A epoxy resin with an epoxy equivalent of 750 and bisphenol A with a hydroxyl equivalent of 250.
33 parts by weight of 7 ether resin derived from and epichlorohydrin, 0.8 parts by weight of 2-methylimidazole
Lffls, 30 parts by weight of rutile titanium oxide, 30 parts by weight of glass flakes with an average particle size of 50 μm, 1 part by weight of an acrylic flow control agent consisting of an oligomer of 2-ethylhexyl acrylate, 1 part by weight of N as a silane coupling agent.
, 1 part by weight of Nl-bis(triethoxysilyl)diaminonophenylmethane was added to each, premixed using a high-speed stirrer, melt-kneaded using an extruder, cooled, and pulverized to obtain a powder coating with an average particle size of 60 μm. I got it.
実施例２
実施例１において用いたシランカップリング剤に代えて
、Ｎ、Ｎ’−ビス（トリメ）−Ｎシシリル）ノアミ／ノ
フェニルエーテルを用いた以外は、実施例１と同様にし
て粉体塗料を得た。Example 2 Powder was prepared in the same manner as in Example 1, except that N,N'-bis(trime)-Ncysilyl)noami/nophenyl ether was used in place of the silane coupling agent used in Example 1. Got the paint.
実施例３
実施例１において用いたシランカップリング剤に代えて
Ｎ 、 Ｎ ’−ビス（トリメトキシシリル）ノアミ
７ノフェニルスルホンを用いた以外は、実施例１と同様
にして粉体塗料を得た。Example 3 A powder coating was obtained in the same manner as in Example 1, except that N,N'-bis(trimethoxysilyl)noami7nophenyl sulfone was used in place of the silane coupling agent used in Example 1. Ta.
実施例４
実施例１において用いたシランカップリング剤に代えて
、Ｎ、Ｎ’−ビス（トリメトキシシリル）ノアミノノ゛
フェニルチオエーテルを用いた以外は、実施例１と同様
にして粉体塗料を得た。Example 4 A powder coating was obtained in the same manner as in Example 1, except that N,N'-bis(trimethoxysilyl)noamino phenylthioether was used in place of the silane coupling agent used in Example 1. Ta.
比較例１
実施例１において用いたシランカップリング剤に代えて
、γ−アミ／プロピルトリエトキシシランを用いた以外
は、実施例１と同様にして粉体塗料を得た。Comparative Example 1 A powder coating was obtained in the same manner as in Example 1, except that γ-amino/propyltriethoxysilane was used instead of the silane coupling agent used in Example 1.
各実施例および比較例により得られた粉体塗料を、温度
２４０°Ｃに予熱した熱間圧延鋼板に市電塗装した後、
温度２００°Ｃで５分後加熱して、それぞれ：５１表に
示す厚さの塗膜を得た。After applying the powder coating obtained in each example and comparative example to a hot rolled steel plate preheated to 240°C,
After heating at a temperature of 200° C. for 5 minutes, a coating film having the thickness shown in Table 51 was obtained.
この塗膜の熱塩水吸水率、塩水噴霧武装（ＪＩＳ Ｚ
２３７１による）１０００１時間後の錆の発生状況
、塗膜中の気泡の状況を調べた結果を第１表に示す。The hot salt water absorption rate of this coating film, the salt water spray armament (JIS Z
Table 1 shows the results of investigating the state of rust occurrence and the state of air bubbles in the coating film after 10,001 hours (according to No. 2371).
（以下余白）
第１表より、各実施例のものは、比較例に比べて、熱塩
水吸水率試験、塩水噴霧試験およＶ気泡の発生試験のい
ずれの試験でも極めて優れた結果が得られていることが
認められる。(Left below) From Table 1, it can be seen that the products of each example obtained extremely superior results in all of the hot salt water absorption test, salt water spray test, and V bubble generation test compared to the comparative example. It is recognized that
（ｇ）発明の効果
本発明の耐熱性シランカップリング剤は、分子内にトリ
アルコキシシリル基を２つ以上含む芳香族アミン系のシ
ラン化合物で形成されており、したがって、沸点が高く
、昇華や蒸発が生じにくいから、加熱加工処理の際の気
泡の発生が極力抑制される結果、本来のカップリング（
戊能を充分に発現して接着性が着しく向上し、これによ
って絶縁性や防食性が至極改善される結果を有するので
ある。(g) Effects of the Invention The heat-resistant silane coupling agent of the present invention is formed from an aromatic amine-based silane compound containing two or more trialkoxysilyl groups in the molecule, and therefore has a high boiling point and is resistant to sublimation. Since evaporation is difficult to occur, the generation of bubbles during heat processing is suppressed to the utmost, and the original coupling (
The adhesive properties are sufficiently developed and the adhesive properties are significantly improved, resulting in extremely improved insulation properties and anti-corrosion properties.
Claims (1)
芳香族アミン系のシラン化合物から成る耐熱性シランカ
ップリング剤。(1) A heat-resistant silane coupling agent comprising an aromatic amine-based silane compound containing two or more trialkoxysilyl groups in the molecule.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13344986A JPS62290736A (en) | 1986-06-09 | 1986-06-09 | Heat-resistant silane coupling agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13344986A JPS62290736A (en) | 1986-06-09 | 1986-06-09 | Heat-resistant silane coupling agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62290736A true JPS62290736A (en) | 1987-12-17 |
Family
ID=15105033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13344986A Pending JPS62290736A (en) | 1986-06-09 | 1986-06-09 | Heat-resistant silane coupling agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62290736A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5539031A (en) * | 1992-08-26 | 1996-07-23 | Armco Inc. | Metal substrate with enhanced corrosion resistance and improved paint adhesion |
-
1986
- 1986-06-09 JP JP13344986A patent/JPS62290736A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5539031A (en) * | 1992-08-26 | 1996-07-23 | Armco Inc. | Metal substrate with enhanced corrosion resistance and improved paint adhesion |
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