JP3710607B2 - Composition comprising mixture of sulfur-containing organosilicon compound, surface treatment agent containing the same, and resin additive composition - Google Patents

Description

【０００９】
（ただし、一般式（１）において、Ｒ¹、Ｒ²は炭素数１〜５のアルキル基、Ｒ³ は
【００１０】
【化４】

【００１１】
基であり、Ｒ⁴、Ｒ⁵は炭素数１〜５のアルキル基またはアルコキシアルキル基であり、ｍは１〜１０、ｎは１〜３、ｌは２〜１０の整数である。）
（２）前記（１）の組成物を有効成分とする表面処理剤、
（３）前記（１）の組成物を有効成分とする樹脂添加剤、
にある。
【００１２】
以下に本発明をさらに詳細に説明する。
【００１３】
本発明の組成物は、上記（１）および（２）の化合物が、４０〜２００℃に加温することによって以下の２種類の反応をし、本発明の効果を十分に発揮されるものと考えられる。
【００１４】
（ａ）エポキシ基とアミノ基の反応（下記反応式（３）参照）
（ｂ）（ａ）によって生じたＯＨ基とアルコキシシリル基の反応（下記反応式 （４）参照）
これらの反応はＦＴ−ＩＲ、ＮＭＲより確認できる。
【００１５】
【化５】

【００１６】
すなわち、主成分は以下に示す構造式（５）〜（７）であるものと推定される。
【００１７】
【化６】

【００１８】
これらの反応生成物はいずれも本発明の効果に寄与するものであり、分離あるいは除去する必要がない。本発明に係る組成物はジアルキルアミノ基の硬化促進作用、ＳｉＯＲやＳｉＯＳｉオリゴマーの無機物質や有機物質との反応や耐久性とが相乗的に働き本発明の効果を発揮しているものと考えられる。
【００１９】
本発明の組成物は４０〜２００℃に加温した前記式（１）で表されるジアルキルアミン中に前記式（２）で表されるエポキシシランを滴下させた後、過剰量のジアルキルアミンや上記反応式（４）で示せる反応により生成したアルコールを減圧下で除去することにより製造できる。
【００２０】
この反応は、前記ジアルキルアミンに対して０．１〜１０倍モルの前記エポキシシランを用いることにより製造することができる。加熱時間は滴下後、５分〜２時間程度撹拌すれば十分である。この反応は特には溶媒を必要としないが、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。
【００２１】
上記一般式（１）におけるＲ¹、Ｒ²は炭素数が１〜５のアルキル基であれば、本発明の効果を十分発揮するが、樹脂の硬化剤または硬化促進剤としてアミンが効果的に作用するためには、炭素数が少ない方が好ましい。
【００２２】
また、上記一般式（２）におけるＲ⁴、Ｒ⁵は炭素数が１〜５のアルキル基であるが、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であるが好ましくは１〜５である。
【００２３】
また、上記式（２）に表されているエポキシシランは、下記一般式（８）のエポキシ化合物と一般式（９）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。
【００２４】
【化７】

【００２５】
（ただし、Ｒ⁴、Ｒ⁵、ｍ、ｎは前記と同義。Ｒ⁶は
【００２６】
【化８】

【００２７】
であり、ｌは２〜１０である）
上記ジアルキルアミンとエポキシシランの反応モル比は、ジアルキルアミン１モルに対して、０．１〜１０モルのエポキシ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ジアルキルアミン１モルに対して、メルカプトシランを１モル以下の添加が好ましい。
【００２８】
この反応の反応時間は、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。
【００２９】
上記の反応で得られた組成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特に制限がない。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。
【００３０】
なおこの有機ケイ素化合物の組成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。
【００３１】
上記、本発明の有機ケイ素化合物の組成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。添加は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部に対して０．００１〜５０部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。
【００３２】
【発明の実施の形態】
以下に実施例を示し、本発明をさらに詳細に説明する。
【００３３】
【実施例】
合成例１
エポキシシラン１の合成
【００３４】
【化９】

【００３５】
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。
【００３６】
合成例２
エポキシシラン２の合成
【００３７】
【化１０】

【００３８】
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。
【００３９】
実施例１
組成物１の合成
（エポキシシラン１とジメチルアミンの反応）
ジメチルアミン１３．５ｇ（０．３ｍｏｌ）と上記エポキシシラン１ ３１．１ｇ（０．１ｍｏｌ）を窒素雰囲気にしたオートクレーブ中に入れ、１５０℃で１時間加熱した。反応後、反応混合物中の過剰のジメチルアミンをエバポレーターにより除去し、ジメチルアミノ基を有する組成物１ ３０．７ｇを得た。得られた組成物１の ¹Ｈ−ＮＭＲ、¹³Ｃ−ＮＭＲ、ＦＴ−ＩＲを図７〜９に示す。
【００４０】
実施例２
組成物２の合成
（エポキシシラン２とジメチルアミンの反応）
ジメチルアミン１３．５ｇ（０．３ｍｏｌ）とエポキシシラン２ ２５．４ｇ（０．０７５ｍｏｌ）を窒素雰囲気にしたオートクレーブ中に入れ、１５０℃で１時間加熱した。反応後、反応混合物中の過剰のジメチルアミンをエバポレーターにより除去し、ジメチルアミノ基を有する組成物２ ２８．４ｇを得た。得られた組成物２の ¹Ｈ−ＮＭＲ、¹³Ｃ−ＮＭＲ、ＦＴ−ＩＲを図１０〜１２に示す。
【００４１】
実施例３
金属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）を上記組成物２の０．４％の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を行った。このアルミ合金板２枚をエポキシ樹脂組成物［（エピコート８２８、油化シェルエポキシ製）：１００部、硬化剤としてＨＮ−２２００（メチルテトラヒドロ無水フタル酸、日立化成製）：８０部、硬化促進剤として２−エチル−４−メチルイミダゾール（四国化成製）：１部、硬化条件は１００℃で１時間後、１５０℃で１時間）］により接着し、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１に示す。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または０．４％ ３−アミノ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。
【００４２】
【表１】

【００４３】
実施例４
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（樹脂組成物はエピコート８２８：１００部、ＨＮ−２２００：８０部、上記組成物１または組成物２：１部、硬化条件は１００℃で１時間後、１５０℃で１時間）により接着し、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組成物１または２：１部を２−エチル−４−メチルイミダゾール：１部に変えて同様に評価した。その結果を表２に併せて示した。
【００４４】
【表２】

【００４５】
【発明の効果】
以上説明したように、本発明のいおう含有有機ケイ素化合物の混合物からなる組成物は金属および無機物質の表面処理剤としてこれらと樹脂との接着性を向上させ、また、樹脂添加剤として硬化反応を促進させる作用を有し、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で得られた組成物１の ¹Ｈ−ＮＭＲ。
【図８】同上、¹³Ｃ−ＮＭＲ。
【図９】同上、ＦＴ−ＩＲ。
【図１０】実施例２で得られた組成物２の ¹Ｈ−ＮＭＲ。
【図１１】同上、¹³Ｃ−ＮＭＲ。
【図１２】同上、ＦＴ−ＩＲ。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a surface treatment agent for improving the adhesion between a metal such as copper, steel and aluminum, or glass fibers, silica, aluminum oxide, aluminum hydroxide and the like and a resin, or a resin such as an epoxy resin. The present invention relates to a resin additive for accelerating the curing of the resin and improving the mechanical strength.
[0002]
[Prior art]
Boards for electronic devices are made by heating and pressing copper foil and paper-phenolic resin-impregnated substrate or glass-epoxy resin-impregnated substrate to form a copper-clad laminate, and then etching to form a circuit network. It is made by mounting elements such as semiconductor devices.
[0003]
In these processes, bonding of the copper foil and the substrate, heating, immersion in an acid or alkaline solution, application of resist ink, soldering, and the like are performed, and thus various performances are required. In order to satisfy these requirements, the copper foil has a brass layer forming treatment (Japanese Patent Publication Nos. 51-35711 and 54-6701), chromate treatment, zinc or zinc-chromium group consisting of zinc oxide and chromium oxide. Mixture coating treatment (Japanese Patent Publication No. 58-7077), silane coupling agent treatment, and the like have been studied. The resin satisfies the above-mentioned required characteristics by changing the type of resin itself, the type of curing agent, and its blending amount, and additives. Further, surface treatments such as silane coupling agents are being studied for glass fibers. However, recently, since the printed circuit has become denser, the characteristics required for the board for the electronic device to be used have become increasingly severe.
[0004]
In addition, casting materials for electrical insulation used for sealing high-voltage / high-capacity equipment such as power plants and semiconductors are composite materials in which an epoxy resin matrix is filled with inorganic substances such as silica and alumina. is there. These materials are required to have various electrical and mechanical properties. In order to satisfy these properties, it is necessary to improve the adhesion between the inorganic substance and the resin. As countermeasures, it has been proposed to add a silane coupling agent to the resin or to treat the surface of an inorganic substance with a silane coupling agent. However, further improvement of the resin / inorganic substance interface is required.
[0005]
[Problems to be solved by the invention]
The present invention can meet such a demand. Namely, a composition containing a novel organosilicon compound capable of improving the adhesion between a metal such as copper, steel and aluminum, or an inorganic substance such as glass fiber, silica and alumina, and a resin, and a surface treatment agent using the composition Alternatively, it is an object to provide a resin additive.
[0006]
[Means for Solving the Problems]
As a result of earnest research, the present inventor can improve the adhesion with a resin when the composition obtained by reacting a specific reactant is surface-treated with a metal or an inorganic substance, It has been found that even when added to a resin molded product such as an epoxy resin, the curing reaction is accelerated and the mechanical strength of the resin is improved.
[0007]
The present invention has been made on the basis of such findings, the gist of which is as follows:
(1) A sulfur-containing organosilicon compound obtained by reacting a dialkylamine represented by the following general formula (1) and an epoxysilane represented by the following general formula (2) by heating at 40 ° C. to 200 ° C. A composition comprising a mixture of
[0008]
[Chemical 3]

[0009]
(In the general formula (1), R ¹ and R ² are alkyl groups having 1 to 5 carbon atoms, and R ³ is
[Formula 4]

[0011]
R ⁴ and R ⁵ are alkyl groups or alkoxyalkyl groups having 1 to ⁵ carbon atoms, m is 1 to 10, n is 1 to 3, and l is an integer of 2 to 10. )
(2) a surface treatment agent comprising the composition of (1) as an active ingredient,
(3) A resin additive comprising the composition of (1) as an active ingredient,
It is in.
[0012]
The present invention is described in further detail below.
[0013]
In the composition of the present invention, the compounds of the above (1) and (2) undergo the following two kinds of reactions by heating to 40 to 200 ° C., and the effects of the present invention are sufficiently exhibited. Conceivable.
[0014]
(A) Reaction of epoxy group and amino group (see the following reaction formula (3))
(B) Reaction of OH group and alkoxysilyl group generated by (a) (see the following reaction formula (4))
These reactions can be confirmed by FT-IR and NMR.
[0015]
[Chemical formula 5]

[0016]
That is, it is presumed that the main components are structural formulas (5) to (7) shown below.
[0017]
[Chemical 6]

[0018]
All of these reaction products contribute to the effects of the present invention and do not need to be separated or removed. The composition according to the present invention is considered to exhibit the effects of the present invention by synergistically working with the hardening promoting action of dialkylamino groups, the reaction of SiOR and SiOSi oligomers with inorganic and organic substances and durability. .
[0019]
In the composition of the present invention, an epoxysilane represented by the formula (2) is dropped into the dialkylamine represented by the formula (1) heated to 40 to 200 ° C., and then an excess amount of the dialkylamine or It can manufacture by removing the alcohol produced | generated by reaction shown by the said Reaction formula (4) under reduced pressure.
[0020]
This reaction can be produced by using 0.1 to 10 moles of the epoxysilane with respect to the dialkylamine. It is sufficient that the heating time is stirred for about 5 minutes to 2 hours after dropping. This reaction does not particularly require a solvent, but an organic solvent such as chloroform, dioxane, methanol or ethanol may be used as a reaction solvent. In addition, since this reaction dislikes moisture, it is preferable to perform in a gas atmosphere containing no moisture such as dry nitrogen or argon so that moisture is not mixed.
[0021]
If R ¹ and R ² in the general formula (1) are alkyl groups having 1 to 5 carbon atoms, the effects of the present invention are sufficiently exerted, but amines are effective as curing agents or curing accelerators for resins. In order to act, it is preferable that the number of carbon atoms is small.
[0022]
In the general formula (2), R ⁴ and R ⁵ are alkyl groups having 1 to 5 carbon atoms. In particular, the ease of synthesis is the methyl group from the viewpoint of silane hydrolysis and condensation. Or an ethyl group is preferable. Further, n is 1 to 3, but 2 or 3 is preferable because n has a higher reactivity with a metal, an inorganic substance or a resin, or a higher crosslinkability, so that the adhesion characteristics are improved. Moreover, m is 1-10, but preferably 1-5.
[0023]
The epoxysilane represented by the above formula (2) can be produced by reacting an epoxy compound of the following general formula (8) with a mercaptosilane of the general formula (9) in the presence of a radical initiator. it can.
[0024]
[Chemical 7]

[0025]
(However, R ⁴ , R ⁵ , m and n are as defined above. R ⁶ is
[Chemical 8]

[0027]
And l is 2 to 10)
The reaction molar ratio of the dialkylamine and epoxysilane can be produced by reacting 0.1 to 10 moles of epoxysilane with respect to 1 mole of dialkylamine. Since a polymerization reaction between them occurs as a side reaction, it is preferable to add 1 mol or less of mercaptosilane with respect to 1 mol of dialkylamine.
[0028]
About several minutes to several hours is sufficient for the reaction time of this reaction. This reaction does not particularly require a solvent, but an organic solvent such as toluene, chloroform, dioxane, methanol, ethanol or the like may be used as a reaction solvent. In addition, since this reaction dislikes a water | moisture content, it is preferable to carry out in the gas atmosphere which does not contain moisture, such as dry nitrogen and argon, so that a water | moisture content may not mix.
[0029]
When the composition obtained by the above reaction is used as a surface treatment agent for a metal or inorganic substance, the metal or inorganic substance is not particularly limited. For example, for metals, copper, iron, aluminum, zinc and the like or alloys thereof, and for inorganic substances, glass fibers, silica, aluminum oxide, aluminum hydroxide, magnesium oxide, barium carbonate, talc and the like. The surface treatment agent may be applied as it is, but it may be diluted with a solvent such as water, methanol, ethanol, acetone, ethyl acetate, toluene or the like so as to be 0.001 to 20% by weight, or sprayed with metal. Or it is convenient and preferable to apply | coat by the method of immersing an inorganic substance.
[0030]
In addition, although the composition of this organosilicon compound may be used independently, you may mix and use with another silane or a titanate coupling agent and a rust preventive agent.
[0031]
When the above-described composition of the 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 effectively acts as a curing accelerator and can fully exhibit the effects of the present invention. The addition may be carried out as it is, or may be added after being dissolved in an alcohol, aromatic or aliphatic organic solvent. If the addition amount is 0.001 to 50 parts with respect to 100 parts of the resin, the effect of the present invention can be sufficiently exhibited. In addition, you may use the novel organosilicon compound of this invention together with additives, such as a hardening | curing agent, a silane coupling agent, and a plasticizer.
[0032]
DETAILED DESCRIPTION OF THE INVENTION
The following examples illustrate the present invention in more detail.
[0033]
【Example】
Synthesis example 1
Synthesis of epoxy silane 1
[Chemical 9]

[0035]
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 subjected to epoxy silane 1 by distillation under reduced pressure. (Yield; 54.5 g (yield; 88%), boiling point; 130-134 ° 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 this compound are shown in FIGS.
[0036]
Synthesis example 2
Synthesis of epoxy silane 2
[Chemical Formula 10]

[0038]
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 subjected to epoxysilane 2 by distillation 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 this compound are shown in FIGS.
[0039]
Example 1
Composition 1 (Epoxysilane 1 and dimethylamine reaction)
13.5 g (0.3 mol) of dimethylamine and 31.1 g (0.1 mol) of the above epoxysilane 1 were put in an autoclave in a nitrogen atmosphere and heated at 150 ° C. for 1 hour. After the reaction, excess dimethylamine in the reaction mixture was removed by an evaporator to obtain 30.7 g of a composition 1 having a dimethylamino group. ¹ H-NMR, ¹³ C-NMR, and FT-IR of the obtained Composition 1 are shown in FIGS.
[0040]
Example 2
Synthesis of composition 2 (reaction of epoxysilane 2 and dimethylamine)
13.5 g (0.3 mol) of dimethylamine and 25.4 g (0.075 mol) of epoxysilane 2 were placed in an autoclave in a nitrogen atmosphere and heated at 150 ° C. for 1 hour. After the reaction, excess dimethylamine in the reaction mixture was removed by an evaporator to obtain 28.4 g of a composition 2 having a dimethylamino group. ¹ H-NMR, ¹³ C-NMR, and FT-IR of the obtained Composition 2 are shown in FIGS.
[0041]
Example 3
Application as a metal surface treatment agent An aluminum alloy plate (A2024P specified in JIS H4000, manufactured by Nippon Test Panel, thickness 1.6 mm, 25 × 100 mm) is used in a 0.4% methanol solution of the above composition 2. After soaking, the surface treatment was performed by drying with a dryer. Epoxy resin composition [(Epicoat 828, made by oiled shell epoxy): 100 parts, HN-2200 (methyltetrahydrophthalic anhydride, manufactured by Hitachi Chemical Co., Ltd.): 80 parts, hardening accelerator 2-ethyl-4-methylimidazole (manufactured by Shikoku Chemicals): 1 part, curing conditions are 1 hour at 100 ° C. and 1 hour at 150 ° C.)], and a tensile shear adhesion test is performed according to JIS K6850 It was. The results are shown in Table 1. For comparison, an untreated aluminum alloy plate and an aluminum alloy plate treated with a methanol solution of 0.4% 3-glycidoxypropyltrimethoxysilane or 0.4% 3-aminopropyltrimethoxysilane were similarly evaluated. . The results are also shown in Table 1.
[0042]
[Table 1]

[0043]
Example 4
Application as additive to resin Two untreated aluminum alloy plates were bonded to an epoxy resin composition (the resin composition was Epicoat 828: 100 parts, HN-2200: 80 parts, Composition 1 or composition above) 2: 1 parts, after curing at 100 ° C. for 1 hour and at 150 ° C. for 1 hour), a tensile shear adhesion test was conducted according to JIS K6850. The results are shown in Table 2. For comparison, the composition 1 or 2: 1 part in the epoxy resin composition was changed to 1 part of 2-ethyl-4-methylimidazole and evaluated in the same manner. The results are also shown in Table 2.
[0044]
[Table 2]

[0045]
【The invention's effect】
As described above, the composition comprising the mixture of the organosilicon compound containing sulfur of the present invention improves the adhesion between these and a resin as a surface treatment agent for metals and inorganic substances, and performs a curing reaction as a resin additive. It has the effect of promoting and can improve the adhesion between the metal and the resin.
[Brief description of the drawings]
1 is a ¹ H-NMR spectrum of epoxysilane 1 obtained in Synthesis Example 1. FIG.
FIG. 2 Same as above, ¹³ C-NMR.
FIG. 3 is the same as above, FT-IR.
4 is a ¹ H-NMR spectrum of epoxysilane 2 obtained in Synthesis Example 2. FIG.
FIG. 5 Same as above, ¹³ C-NMR.
FIG. 6 is the same as above, FT-IR.
7 is ¹ H-NMR of the composition 1 obtained in Example 1. FIG.
FIG. 8 Same as above, ¹³ C-NMR.
FIG. 9 is the same as above, FT-IR.
10 is ¹ H-NMR of the composition 2 obtained in Example 2. FIG.
FIG. 11 Same as above, ¹³ C-NMR.
FIG. 12 is the same as above, FT-IR.

Claims (3)

From a mixture of organosilicon compounds containing sulfur obtained by heating and reacting a dialkylamine represented by the following general formula (1) and an epoxysilane represented by the following general formula (2) at 40 ° C. to 200 ° C. Composition.

(However, in the general formula ^{(1), R 1, R} 2 is an alkyl group having 1 to 5 carbon atoms, R ³ is

R ⁴ and R ⁵ are alkyl groups or alkoxyalkyl groups having 1 to ⁵ carbon atoms, m is 1 to 10, n is 1 to 3, and l is an integer of 2 to 10. ) A surface treatment agent comprising the composition according to claim 1 as an active ingredient. A resin additive comprising the composition of claim 1 as an active ingredient.

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