JP3555825B2 - Novel organosilicon compound, method for producing the same, surface treating agent and resin additive using the same - Google Patents

Description

【００１０】
（ただし、Ｒ^１、Ｒ^２、Ｒ^３は水素、アルキル基、ビニル基、フェニル基又はベンジル基であり、Ｒ^４、Ｒ^５はアルキル基又はアルコキシアルキル基であり、Ｒ^７は
【００１１】
【化５】

【００１２】
基であり、ｌは２〜１０である。ｍは１〜１０、ｎは１〜３の整数である。ただし、Ｒ^２、Ｒ^３は結合してベンゼン環になっても良く、この場合はベンズイミダゾール基となる。）
（２）下記一般式（２）で表されるイミダゾール化合物と下記一般式（３）で表されるエポキシシランを４０〜１５０℃で反応させることを特徴とする前記（１）記載の有機ケイ素化合物の製造方法、
【００１３】
【化６】

【００１４】
（ただし、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^７、ｍ、ｎは一般式（１）と同義）
（３）前記（１）記載の一般式（１）で表される有機ケイ素化合物を有効成分とする表面処理剤、
（４）前記（１）記載の一般式（１）で表される有機ケイ素化合物を有効成分とする樹脂添加剤、
にある。
【００１５】
以下に本発明をさらに詳細に説明する。
【００１６】
上記一般式（１）におけるＲ^１、Ｒ^２、Ｒ^３は水素、アルキル基、ビニル基又はベンジル基であれば本発明の効果を十分に発揮する。ただし、これらの置換基は使用する用途によって適したものを選定する必要がある。すなわち、フィラーや金属等に水溶液で表面処理したい場合は、水素または炭素数の少ないアルキル基が溶解性の点で好ましい。また、樹脂に添加する場合は、その樹脂と相溶性が高い置換基を選定する必要がある。
【００１７】
上記一般式（１）におけるＲ^４、Ｒ^５はアルコキシアルキル基またはアルキル基であり、それらのアルキル基の炭素数は１〜５が好ましく、特には合成の容易性はシランの加水分解、縮合のし易さの点からメチル基またはエチル基が好適である。また、ｎは１〜３であるが、金属、無機物質や樹脂との反応性や架橋性の高い方が接着特性が向上するため、ｎは２または３が好適である。また、ｍは１〜１０、ｌは２〜１０である。
【００１８】
本発明の上記新規有機ケイ素化合物（１）は、下記反応式（４）で表される反応により合成される。すなわち、４０〜１５０℃に加熱したイミダゾール化合物の中にエポキシシランを滴下することにより製造することができる。
【００１９】
【化７】

【００２０】
（ただし、上記反応式（４）において、各記号は前記と同義）
また、上記反応式（４）における反応物質エポキシシランは、下記一般式（５）のエポキシ化合物と一般式（６）のメルカプトシランをラジカル開始剤の存在下で反応させることにより製造することができる。
【００２１】
【化８】

【００２２】
（ただし、Ｒ^４、Ｒ^５、ｍ、ｎは前記と同義。Ｒ^８は
【００２３】
【化９】

【００２４】
であり、ｌは２〜１０である。）
上記反応式（４）のイミダゾール化合物とエポキシシランの反応モル比は、イミダゾール化合物１モルに対して、０．１〜１０モルのエポキシランを反応させることにより製造することができるが、エポキシシランを過剰に添加するとエポキシシラン同士の重合反応も副反応として起こるため、イミダゾール化合物１モルに対してエポキシシランを１モル以下添加するのが好ましい。
【００２５】
新規有機ケイ素化合物を合成するための反応時間は、数分〜数時間程度で十分である。この反応は特には溶媒を必要としないが、トルエン、クロロホルム、ジオキサン、メタノール、エタノール等の有機溶剤を反応溶媒として用いてもよい。なおこの反応は、水分を嫌うので水分が混入しないように、乾燥した窒素、アルゴン等の水分を含まない気体の雰囲気下で行うことが好ましい。
【００２６】
また、上記の反応においては副反応として、ＯＨ基とＳｉＯＲ^４基が分子内または分子間で反応し、環状化合物またはオリゴマーを生成する反応もおこる。これらの副反応生成物は、本発明に係る新規有機ケイ素化合物と同様に蒸留、カラムクロマトグラフィー等の既知の手段によって単離されるうるが、表面処理剤や樹脂の添加剤として用いる場合には、これらの化合物は必ずしも単離する必要がなく、反応混合物のまま用いてもよい。
【００２７】
上記、新規有機ケイ素化合物を金属または無機物質の表面処理剤として用いる場合、その金属または無機物質にはとくに制限がない。たとえば、金属では、銅、鉄、アルミニウム、亜鉛等またはそれらの合金、無機物質ではガラス繊維、シリカ、酸化アルミニウム、水酸化アルミニウム、酸化マグネシウム、炭酸バリウム、タルク等である。表面処理剤は、そのまま塗布してもよいが、水、メタノール、エタノール、アセトン、酢酸エチル、トルエン等の溶剤で０．００１〜２０重量％になるように希釈して噴霧するか、この液に金属または無機物質を浸漬させる方法で塗布することが簡便で好ましい。
【００２８】
なおこの新規有機ケイ素化合物は単独で用いてもよいが、他のシランまたはチタネートカップリング剤、防錆剤と混合して用いてもよい。
【００２９】
上記、本発明の新規有機ケイ素化合物を樹脂添加剤として用いる場合、その樹脂には特に制限がなく、熱可塑性樹脂でも熱硬化性樹脂でもよいが、特にはエポキシ樹脂に添加すると硬化剤または硬化促進剤として効果的に作用し、本発明の効果を十分に発揮することができる。本発明の新規有機ケイ素化合物は樹脂中にそのまま添加してもアルコール系、芳香族系、脂肪族系有機溶剤等に溶解して添加してもよい。添加量は樹脂１００に対して０．００１〜５０添加すれば本発明の効果を十分発揮できる。なお本発明の新規有機ケイ素化合物は、硬化剤、シランカップリング剤、可塑剤等の添加剤等と併用してもよい。
【００３０】
【発明の実施の形態】
合成例１
エポキシシラン１の合成
【００３１】
【化１０】

【００３２】
アリルグリシジルエーテル２２．８ｇ（０．２ｍｏｌ）と３−メルカプトプロピルトリメトキシシラン３９．３ｇ（０．２ｍｏｌ）とＡＩＢＮ１．０ｇを混合し、６０℃、２時間加熱した後、減圧蒸留によりエポキシシラン１を得た（収量；５４．５ｇ（収率；８８％）、沸点；１３０〜１３４℃／０．１ｍｍＨｇ）。得られた化合物はＦＴ−ＩＲ、ＮＭＲにより同定した。本化合物の ^１Ｈ−ＮＭＲ、^１３Ｃ−ＮＭＲ、ＦＴ−ＩＲスペクトルを図１〜３に示す。
【００３３】
合成例２
エポキシシラン２の合成
【００３４】
【化１１】

【００３５】
メタクリル酸グリシジル２８．４ｇ（０．２ｍｏｌ）と３−メルカプトプロピルトリメトキシシラン３９．３ｇ（０．２ｍｏｌ）とＡＩＢＮ１．０ｇを混合し、６０℃、２時間加熱した後、減圧蒸留によりエポキシシラン２を得た（収量；９．５ｇ（収率；１４％）、沸点；１４７〜１５４℃／０．１ｍｍＨｇ）。得られた化合物はＦＴ−ＩＲ、ＮＭＲにより同定した。本化合物の ^１Ｈ−ＮＭＲ、^１３Ｃ−ＮＭＲ、ＦＴ−ＩＲスペクトルを図４〜６に示す。
【００３６】
実施例１
新規有機ケイ素化合物１の合成
【００３７】
【化１２】

【００３８】
１Ｈ−イミダゾール６８．１ｇ（１ｍｏｌ）を９５℃に加熱し、アルゴン雰囲気で撹拌しながら合成例１で合成したエポキシシラン１ ３１０．５ｇ（１ｍｏｌ）をゆっくり滴下した。滴下終了後、さらに９５℃で１時間反応させ、上記式で表されるイミダゾール基含有新規有機ケイ素化合物１を合成した。得られた化合物は、ＦＴ−ＩＲよりＯＨ基を確認し、 ^１Ｈ−ＮＭＲと^１３Ｃ−ＮＭＲにより同定した。その結果を図７〜９に示す。
【００３９】
実施例２
新規有機ケイ素化合物２の合成
【００４０】
【化１３】

【００４１】
１Ｈ−イミダゾール６８．１ｇ（１ｍｏｌ）を９５℃に加熱し、アルゴン雰囲気で撹拌しながら合成例２で合成したエポキシシラン２ ３３８．６ｇ（１ｍｏｌ）をゆっくり滴下した。滴下終了後、さらに９５℃で１時間反応させ、上記式で表されるイミダゾール基含有新規有機ケイ素化合物２を合成した。得られた化合物は、ＦＴ−ＩＲよりＯＨ基を確認し、 ^１Ｈ−ＮＭＲと^１３Ｃ−ＮＭＲにより同定した。その結果を図１０〜１２に示す。
【００４２】
実施例３
表面処理剤としての適用
アルミ合金板（ＪＩＳ Ｈ４０００に規定するＡ２０２４Ｐ、日本テストパネル製、厚さ１．６ｍｍ、２５×１００ｍｍ）を上記新規有機ケイ素化合物１の０．４％メタノール溶液に浸漬した後、ドライヤーで乾燥することにより表面処理した。この表面処理したアルミ合金板２枚をエポキシ樹脂組成物［エピコート８２８（エポキシ樹脂、油化シェルエポキシ製）：１００部、ジシアンジアミド（関東化学（株）製］：５部、２−エチル−４−メチルイミダゾール（四国化成製）：１部］により１００℃で１時間＋１５０℃で１時間の硬化条件で接着し、ＪＩＳ Ｋ６８５０に準じて引張り剪断接着試験を行った。また比較として未処理のアルミ合金板、０．４％３−グリシドキシプロピルトリメトキシシランのメタノール溶液で処理したアルミ合金板についても同様に評価した。その結果を表１に併せて示した。
【００４３】
【表１】

【００４４】
樹脂への添加剤としての適用
未処理のアルミ合金板２枚をエポキシ樹脂組成物［エピコート８２８：１００部、ジシアンジアミド（関東化学製）：５部、上記新規有機ケイ素化合物２：１部］により１００℃で１時間＋１５０℃で１時間の硬化条件で接着し、ＪＩＳ Ｋ６８５０に準じて引張り剪断接着試験を行った。その結果を表２に示す。また比較としてエポキシ樹脂組成物中の上記新規有機ケイ素化合物１部に代えて、２−エチル−４−メチルイミダゾール１部を用いて同様に評価した。その結果を表２に併せて示した。
【００４５】
【表２】

【００４６】
【発明の効果】
以上説明したように、本発明の組成物は表面処理剤、樹脂添加剤として金属と樹脂との接着性を改善することができる。
【図面の簡単な説明】
【図１】合成例１で得られたエポキシシラン１の ^１Ｈ−ＮＭＲ。
【図２】同上、^１３Ｃ−ＮＭＲ。
【図３】同上、ＦＴ−ＩＲ。
【図４】合成例２で得られたエポキシシラン２の ^１Ｈ−ＮＭＲ。
【図５】同上、^１３Ｃ−ＮＭＲ。
【図６】同上、ＦＴ−ＩＲ。
【図７】実施例１で得られた本発明に係る新規有機ケイ素化合物１の ^１Ｈ−ＮＭＲ。
【図８】同上、^１３Ｃ−ＮＭＲ。
【図９】同上、ＦＴ−ＩＲ。
【図１０】実施例２で得られた本発明に係る新規有機ケイ素化合物２の ^１Ｈ−ＮＭＲ。
【図１１】同上、^１３Ｃ−ＮＭＲ。
【図１２】同上、ＦＴ−ＩＲ。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a surface treatment agent for improving the adhesion between a resin such as a metal such as copper, steel and aluminum or glass fiber, an inorganic substance such as silica, aluminum oxide and aluminum hydroxide, and a resin such as an epoxy resin. The present invention relates to a resin additive for improving the mechanical strength of a resin and an organosilicon compound useful therefor.
[0002]
[Prior art]
Boards for electronic equipment are made by heating and pressing copper foil and paper-phenol resin impregnated base material or glass-epoxy resin impregnated base material to create a copper-clad laminate, and then etching to form a circuit network. It is manufactured by mounting an element such as a semiconductor device on the substrate.
[0003]
In these processes, various performances are required because bonding between the copper foil and the base material, heating, immersion in an acid or alkali solution, application of a resist ink, soldering, and the like are performed. In order to satisfy these requirements, the copper foil is subjected to a brass layer forming treatment (JP-B-51-35711 and JP-B-54-6701), a chromate treatment, and a zinc-chromium group comprising zinc or zinc oxide and chromium oxide. A mixture coating treatment (Japanese Patent Publication No. 58-7077), a silane coupling agent treatment, and the like have been studied. In addition, the resin satisfies the above-mentioned required characteristics by changing the type and the amount of the resin and the curing agent, and by adding additives. Surface treatment of glass fibers with a silane coupling agent or the like is being studied. However, recently, as printed circuits are becoming more and more compact, characteristics required for boards for electronic devices to be used are becoming increasingly severe.
[0004]
In order to cope with the improvement in etching accuracy accompanying this, a further lower surface roughness (low profile) is required on a roughened surface (M surface) bonded to a prepreg of copper foil. However, on the other hand, the surface roughness of the M surface has an anchor effect in bonding with the prepreg, so that the requirement of the low profile for the M surface and the improvement of the adhesive force are in a trade-off relationship, and the low profile It is necessary to compensate for the reduction in the anchor effect by improving the adhesive force by another means.
[0005]
Also, the casting material for electrical insulation used for sealing high-voltage, high-capacity equipment such as power plants and semiconductors is a composite material in which an epoxy resin matrix is filled with an inorganic substance such as silica or alumina. is there. These materials are required to have various electrical and mechanical properties, and in order to satisfy those properties, it is necessary to improve the adhesion between the inorganic substance and the resin. As measures against this, it has been proposed to add a silane coupling agent to the resin or to perform a surface treatment of an inorganic substance with the silane coupling agent, but further improvement of the resin / inorganic substance interface is required.
[0006]
[Problems to be solved by the invention]
The present invention can respond to such a request. That is, a novel organosilicon compound capable of improving the adhesion between an inorganic substance such as copper, metal such as steel and aluminum or glass fiber, silica, aluminum oxide, and aluminum hydroxide and a resin, a method for producing the same, and a method for producing the same. It is an object of the present invention to provide a used surface treatment agent or resin additive.
[0007]
[Means for Solving the Problems]
As a result of intensive research, the present inventor has found that when the novel organosilicon compound represented by the general formula (1) is subjected to a surface treatment on a metal or an inorganic substance, the adhesion to a resin can be improved, It has been found that even when added to a resin such as a resin, the curing reaction is promoted and the mechanical strength is improved.
[0008]
The present invention has been made based on such findings, the gist of which is
(1) a novel organosilicon compound represented by the following general formula (1),
[0009]
Embedded image

[0010]
(However, R ¹ , R ² , and R ³ are hydrogen, an alkyl group, a vinyl group, a phenyl group, or a benzyl group, R ⁴ and R ⁵ are an alkyl group or an alkoxyalkyl group, and R ⁷ is
Embedded image

[0012]
And l is 2-10. m is an integer of 1 to 10, and n is an integer of 1 to 3. However, R ² and R ³ may combine to form a benzene ring, and in this case, a benzimidazole group. )
(2) The organosilicon compound according to (1), wherein the imidazole compound represented by the following general formula (2) and the epoxysilane represented by the following general formula (3) are reacted at 40 to 150 ° C. Manufacturing method,
[0013]
Embedded image

[0014]
(However, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁷ , m and n have the same meanings as in the general formula (1))
(3) a surface treating agent comprising, as an active ingredient, an organosilicon compound represented by the general formula (1) described in (1);
(4) a resin additive containing an organosilicon compound represented by the general formula (1) according to the above (1) as an active ingredient;
It is in.
[0015]
Hereinafter, the present invention will be described in more detail.
[0016]
If R ¹ , R ² , and R ³ in the general formula (1) are hydrogen, an alkyl group, a vinyl group, or a benzyl group, the effects of the present invention are sufficiently exhibited. However, it is necessary to select these substituents depending on the intended use. That is, when it is desired to perform a surface treatment on a filler, a metal, or the like with an aqueous solution, hydrogen or an alkyl group having a small number of carbon atoms is preferable in terms of solubility. When adding to a resin, it is necessary to select a substituent having high compatibility with the resin.
[0017]
R ⁴ and R ⁵ in the general formula (1) are each an alkoxyalkyl group or an alkyl group, and the alkyl group preferably has 1 to 5 carbon atoms. A methyl group or an ethyl group is preferable from the viewpoint of easiness. In addition, n is 1 to 3. However, n is preferably 2 or 3, since the higher the reactivity or crosslinkability with a metal, an inorganic substance, or a resin improves the adhesive property. Further, m is 1 to 10, and l is 2 to 10.
[0018]
The novel organosilicon compound (1) of the present invention is synthesized by a reaction represented by the following reaction formula (4). That is, it can be produced by dropping epoxysilane into an imidazole compound heated to 40 to 150 ° C.
[0019]
Embedded image

[0020]
(However, in the above reaction formula (4), each symbol is as defined above)
The reactive substance epoxysilane in the above reaction formula (4) can be produced by reacting an epoxy compound of the following general formula (5) with a mercaptosilane of the general formula (6) in the presence of a radical initiator. .
[0021]
Embedded image

[0022]
(However, R ⁴ , R ⁵ , m and n are as defined above. R ⁸ is
Embedded image

[0024]
And 1 is 2 to 10. )
The reaction molar ratio of the imidazole compound of the above reaction formula (4) and the epoxysilane can be produced by reacting 0.1 to 10 mol of epoxylane with respect to 1 mol of the imidazole compound. If added in excess, the polymerization reaction between the epoxysilanes also occurs as a side reaction, so it is preferable to add 1 mol or less of epoxysilane to 1 mol of the imidazole compound.
[0025]
The reaction time for synthesizing the novel organosilicon compound is from several minutes to several hours. This reaction does not particularly require a solvent, but an organic solvent such as toluene, chloroform, dioxane, methanol, or ethanol may be used as a reaction solvent. Note that this reaction is preferably performed in an atmosphere of a gas containing no moisture, such as dry nitrogen or argon, so as not to mix moisture because it dislikes moisture.
[0026]
In the above reaction, as a side reaction, an OH group and a SiOR ⁴ group react intramolecularly or intermolecularly to generate a cyclic compound or oligomer. These side reaction products can be isolated by known means such as distillation and column chromatography as in the case of the novel organosilicon compound according to the present invention, but when used as a surface treatment agent or an additive for a resin, These compounds do not necessarily need to be isolated and may be used as a reaction mixture.
[0027]
When the novel organosilicon compound is used as a surface treatment agent for a metal or inorganic substance, the metal or inorganic substance is not particularly limited. For example, metals include copper, iron, aluminum, zinc and the like or alloys thereof, and inorganic substances include glass fiber, silica, aluminum oxide, aluminum hydroxide, magnesium oxide, barium carbonate, and talc. The surface treatment agent may be applied as it is, but diluted with a solvent such as water, methanol, ethanol, acetone, ethyl acetate, and toluene so as to be 0.001 to 20% by weight, or sprayed. It is convenient and preferable to apply by a method of dipping a metal or inorganic substance.
[0028]
The novel organosilicon compound may be used alone, or may be used in combination with another silane or titanate coupling agent or rust inhibitor.
[0029]
When the novel organosilicon compound of the present invention is used as a resin additive, the resin is not particularly limited, and may be a thermoplastic resin or a thermosetting resin. It acts effectively as an agent, and can sufficiently exert the effects of the present invention. The novel organosilicon compound of the present invention may be added to the resin as it is, or may be added after being dissolved in an alcohol-based, aromatic-based, or aliphatic-based organic solvent. The effect of the present invention can be sufficiently exhibited by adding 0.001 to 50 to the resin 100. The novel organosilicon compound of the present invention may be used in combination with additives such as a curing agent, a silane coupling agent, and a plasticizer.
[0030]
BEST MODE FOR CARRYING OUT THE INVENTION
Synthesis Example 1
Synthesis of Epoxysilane 1
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[0032]
22.8 g (0.2 mol) of allyl glycidyl ether, 39.3 g (0.2 mol) of 3-mercaptopropyltrimethoxysilane and 1.0 g of AIBN were mixed, heated at 60 ° C. for 2 hours, and then epoxysilane 1 was distilled under reduced pressure. (Yield; 54.5 g (yield; 88%), boiling point: 130 to 134 ° C./0.1 mmHg). The obtained compound was identified by FT-IR and NMR. ¹ H-NMR, ¹³ C-NMR and FT-IR spectra of the present compound are shown in FIGS.
[0033]
Synthesis Example 2
Synthesis of Epoxysilane 2
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[0035]
28.4 g (0.2 mol) of glycidyl methacrylate, 39.3 g (0.2 mol) of 3-mercaptopropyltrimethoxysilane, and 1.0 g of AIBN were mixed, heated at 60 ° C. for 2 hours, and then epoxysilane 2 was distilled under reduced pressure. (Yield: 9.5 g (yield; 14%), boiling point: 147 to 154 ° C./0.1 mmHg). The obtained compound was identified by FT-IR and NMR. ¹ H-NMR, ¹³ C-NMR and FT-IR spectra of the present compound are shown in FIGS.
[0036]
Example 1
Synthesis of novel organosilicon compound 1
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[0038]
68.1 g (1 mol) of 1H-imidazole was heated to 95 ° C., and 310.5 g (1 mol) of the epoxysilane synthesized in Synthesis Example 1 was slowly dropped while stirring in an argon atmosphere. After completion of the dropwise addition, the mixture was further reacted at 95 ° C. for 1 hour to synthesize an imidazole group-containing novel organosilicon compound 1 represented by the above formula. The OH group was confirmed from the obtained compound by FT-IR, and it was identified by ¹ H-NMR and ¹³ C-NMR. The results are shown in FIGS.
[0039]
Example 2
Synthesis of New Organosilicon Compound 2
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[0041]
68.1 g (1 mol) of 1H-imidazole was heated to 95 ° C., and 338.6 g (1 mol) of the epoxysilane 2 synthesized in Synthesis Example 2 was slowly added dropwise while stirring in an argon atmosphere. After completion of the dropwise addition, the mixture was further reacted at 95 ° C. for 1 hour to synthesize an imidazole group-containing novel organosilicon compound 2 represented by the above formula. The OH group was confirmed from the obtained compound by FT-IR, and it was identified by ¹ H-NMR and ¹³ C-NMR. The results are shown in FIGS.
[0042]
Example 3
Application as a surface treatment agent An aluminum alloy plate (A2024P specified by JIS H4000, manufactured by Nippon Test Panel, 1.6 mm, 25 × 100 mm) is a 0.4% methanol solution of the novel organosilicon compound 1 After immersion, the surface was treated by drying with a drier. Two parts of the surface-treated aluminum alloy plate were used as an epoxy resin composition [Epicoat 828 (epoxy resin, manufactured by Yuka Shell Epoxy): 100 parts, dicyandiamide (manufactured by Kanto Chemical Co., Ltd.)]: 5 parts, 2-ethyl-4- Methyl imidazole (manufactured by Shikoku Kasei): 1 part] under a curing condition of 100 ° C. for 1 hour and 150 ° C. for 1 hour, and subjected to a tensile shear adhesion test according to JIS K6850. The plate and an aluminum alloy plate treated with a methanol solution of 0.4% 3-glycidoxypropyltrimethoxysilane were similarly evaluated, and the results are shown in Table 1.
[0043]
[Table 1]

[0044]
Application as an additive to resin Two untreated aluminum alloy plates were treated with an epoxy resin composition [Epicoat 828: 100 parts, dicyandiamide (manufactured by Kanto Kagaku): 5 parts, the novel organosilicon compound 2: 1] And under a curing condition of 100 ° C. for 1 hour and 150 ° C. for 1 hour, a tensile shear adhesion test was performed according to JIS K6850. Table 2 shows the results. For comparison, the same evaluation was conducted using 1 part of 2-ethyl-4-methylimidazole instead of 1 part of the novel organosilicon compound in the epoxy resin composition. The results are also shown in Table 2.
[0045]
[Table 2]

[0046]
【The invention's effect】
As described above, the composition of the present invention can improve the adhesion between a metal and a resin as a surface treatment agent and a resin additive.
[Brief description of the drawings]
[1] ¹ of Synthesis Example epoxysilane 1 obtained in 1 H-NMR.
FIG. 2 Same as above, ¹³ C-NMR.
FIG. 3 Same as above, FT-IR.
FIG. 4 is a ¹ H-NMR of epoxysilane 2 obtained in Synthesis Example 2.
FIG. 5 Same as above, ¹³ C-NMR.
FIG. 6: FT-IR.
FIG. 7 is a ¹ H-NMR of the novel organosilicon compound 1 according to the present invention obtained in Example 1.
FIG. 8: Same as above, ¹³ C-NMR.
FIG. 9: FT-IR.
10 is a ¹ H-NMR of a novel organosilicon compound 2 according to the present invention obtained in Example 2. FIG.
FIG. 11: ¹³ C-NMR.
FIG. 12: FT-IR.

Claims (4)

A novel organosilicon compound represented by the following general formula (1).

(However, R ¹ , R ² and R ³ are hydrogen, an alkyl group, a vinyl group, a phenyl group or a benzyl group, R ⁴ and R ⁵ are an alkyl group or an alkoxyalkyl group, and R ⁷ is

And l is 2-10. m is an integer of 1 to 10, and n is an integer of 1 to 3. However, R ² and R ³ may combine to form a benzene ring, and in this case, a benzimidazole group. ) The method for producing an organosilicon compound according to claim 1, wherein the imidazole compound represented by the following general formula (2) is reacted with the epoxysilane represented by the following general formula (3) at 40 to 150 ° C.

(However, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁷ , m and n have the same meanings as in the general formula (1)) A surface treating agent comprising the organosilicon compound according to claim 1 as an active ingredient. A resin additive comprising the organosilicon compound according to claim 1 as an active ingredient.

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