JPH054994A - Silane coupling agent and glass fiber product for laminate - Google Patents

Abstract

PURPOSE:To provide the title glass fiber product capable of giving highly heat- resistant laminates and also the other title new silane coupling agent used for producing said glass fiber product. CONSTITUTION:The objective silane coupling agent where each at least one vinylbenzyl group and (meth)acryloyl group are bound to the nitrogen atom(s) in a silane coupling agent having at least one amino group, and the other objective glass fiber product treated with this silane coupling agent. The laminates produced using the present glass fiber products cause no measling, having high heat resistance (e.g. excellent in soldering heat resistance).

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a silane coupling agent and a glass fiber product for laminates treated with this silane coupling agent.

[0002]

2. Description of the Related Art Printed circuit boards are widely used in various fields, but in recent years, their importance has been increasing more and more in computer and communication equipment. Among printed circuit boards, those using glass fiber products as a reinforcing material are becoming mainstream from the viewpoint of their performance, and among them, those using a glass fiber woven fabric as a reinforcing material are becoming the mainstream.

The printed circuit board manufactured in this manner becomes a printed circuit board on which a copper foil circuit is formed, and chip parts such as IC and LSI are mounted on the printed circuit board for use in computers, communication devices and the like.

In the case of mounting a chip component on a printed circuit board, conventionally, the legs of the chip are inserted into the through holes, and the chips are dipped in molten solder, and the chips are fixed by soldering. However, when the surface mounting technology comes to be performed with the high integration of chips, the method of fixing the chips is changing from the method of dipping to the molten solder to the method of spotting with the solder paste. In the case of the solder paste method, since it is necessary to instantaneously melt the solder paste to bond and fix the chip, heating at a higher temperature is performed by far infrared irradiation than the method of dipping in the molten solder. It has been confirmed that this heating causes a thermal shock to the printed circuit board itself, and as a result, a small peeling phenomenon called a measling may occur at the intersection of the warp yarn and the weft yarn of the base fabric. When such a peeling phenomenon occurs, the plating solution permeates the peeled portion during through-hole plating, and as a result, circuit conduction occurs in an unnecessary portion. It also affects the roughness of the inner wall of the through hole.

Among these printed circuit boards, a laminated board for a printed circuit board using an unsaturated polyester resin as a matrix resin has been remarkably expanded recently, and this laminated board for a printed circuit board is also immersed in molten solder during a wiring process. Strong heat resistance is required.

Attempts have been made to prepare a composite material with a matrix resin by pretreating a reinforcing material with γ-methacryloxypropyltrimethoxysilane as a silane coupling agent in order to improve heat resistance. Therefore, the heat resistance of the composite material was not sufficient.

Further, it has been attempted to pretreat the reinforcing material with the hydrochloride of N- (vinylbenzyl) -β-aminoethyl-γ-aminopropyltrimethoxysilane, but the amino group portion of this silane compound is treated. Due to poor heat resistance, no sufficient effect has been obtained.

[0008]

SUMMARY OF THE INVENTION Therefore, a first object of the present invention is to provide a novel silane cup which is excellent in heat resistance itself and which can provide a laminated plate having excellent heat resistance when a glass fiber product as a reinforcing material is surface-treated. To provide a ring agent.

A second object of the present invention is to provide a novel glass fiber product for laminates, which can be treated with a silane coupling agent which achieves the first object to give a laminate excellent in heat resistance. To provide.

[0010]

As a result of intensive studies, the present inventors have found that two kinds of radically polymerizable unsaturated groups having different activities together with a silylalkyl group having a silicon atom substituted with a hydrolyzable group Vinyl benzyl group and (meth) acryloyl group], and a silane coupling agent consisting of a monoamine compound and a polyamine compound in which these are substituted in a nitrogen atom, and salts thereof, achieves the first object. It was

That is, the silane coupling agent which achieves the first object of the present invention has one nitrogen atom in the molecule, and has the following groups (a), (b) and (c): Each of them is characterized by comprising the above monoamine compound substituted with one nitrogen atom or a salt thereof. (A) a silylalkyl group in which a silicon atom is substituted with a hydrolyzable group (b) a vinylbenzyl group (c) (meth) acryloyl group, or another silane coupling agent that achieves the first object of the present invention, Having a plurality of nitrogen atoms linked by a divalent organic group in the molecule, the groups represented by the following (a), (b), (c) and (d) are substituted with the plurality of nitrogen atoms. And substituted groups (a), (b), (c),
From a polyamine compound or a salt thereof, in which the number of (d) is represented by n _a , n _b , n _c , and n _d, and n _a ≧ 1, n _b ≧ 1, n _c ≧ 1, and n _d ≧ 0. It is characterized by (A) a silylalkyl group in which a hydrolyzable group is substituted on a silicon atom (b) a vinylbenzyl group (c) (meth) acryloyl group (d) a hydrogen group. It has been found that a glass fiber product for laminates, which has been treated with at least one silane coupling agent composed of these salts, achieves the second object.

Hereinafter, the silane coupling agent and the glass fiber product for laminated plate of the present invention will be sequentially described. The silane coupling agent of the present invention is an aminosilane compound containing halomethylstyrene and (meth) acrylic acid halide (that is, acrylic acid halide and methacrylic acid halide).
It is obtained by reacting.

The aminosilane compound is an aminosilane compound in which a hydrolyzable group (alkoxy group, acyloxy group, etc.) is substituted with a silicon atom, and the silicon atom is linked to a terminal amino group via a divalent organic group. It is preferably used.

As such an aminosilane compound,
The following are listed. (I) 3-aminopropyltriethoxysilane, 3-aminopropylmethyldiethoxysilane, 3-aminopropyldimethylethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminobutyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane Silane, 3-
1 at the end of aminopropyldimethylmethoxysilane
Monoamino-silane compound having only one amino group (ii) N-2-aminoethylaminopropylmethyldimethoxysilane, N-2-aminoethylaminopropylmethyldiethoxysilane, N-2-aminoethylaminopropyltrimethoxysilane , N-2-aminoethylaminopropyltriethoxysilane, N-2-aminoethylaminopropyldimethylmethoxysilane, N-2-aminoethylaminopropyldimethylethoxysilane, N-
Trimethoxysilylpropyldiaminopropane, N-trimethoxysilylpropyldiaminohexane, N-trimethoxysilylpropylphenylenediamine, N-trimethoxysilylpropyldiaminobiphenyl, N-trimethoxysilylpropyldiaminodiphenylmethane,
(Aminoethylaminomethyl) phenethyltrimethoxysilane, N- [2- (vinylbenzylamino) ethyl]
-3-Aminopropyltrimethoxysilane, N, N'-
Bis [3- (trimethoxysilyl) propyl] ethylenediamine, N, N'-bis [3- (trimethoxysilyl) propyl] ethylenediamine, N, N'-bis [3
-(Trimethoxysilyl) propyl] diaminopropane, N, N'-bis [3- (trimethoxysilyl) propyl] diaminohexane, N-trimethoxysilylpropyldiethylenetriamine, N, N'-bis [3- (trimethoxy) Polyamino-silane compound starting material having one amino group at the terminal and one or more amino group in the divalent organic group connecting the terminal amino group and the silicon atom, such as silyl) propyl] diethylenetriamine As the above, when the monoamino-silane compound of the above (i) is used, a silane coupling agent comprising the monoamine compound of the present invention is obtained, and when the polyamino-silane compound of the above (ii) is used, A silane coupling agent comprising the polyamine compound of the invention is obtained.

The above aminosilane compound is a dehydrohalogenation reaction of a haloalkylalkoxysilane and an amine,
It can be obtained by a known method such as a hydrosilylation reaction between an amino compound having an unsaturated double bond and an alkoxysilane.

Examples of the halomethylstyrene used for the reaction with the above aminosilane compound include methyl chloride styrene, methyl bromide styrene, methyl iodide styrene and the like, and methyl chloride styrene is practically convenient.

As the (meth) acrylic acid halide, acrylic acid chloride and methacrylic acid chloride are practically convenient.

The reaction can be carried out in an organic solvent which is inert to the raw materials. As such a solvent, for example, ethers such as dioxane, tetrahydrofuran and diethylene glycol diethyl ether, and aromatic hydrocarbons such as toluene and xylene can be used. It is desirable to use these solvents in a dry state. When the content of water is high, the alkoxy groups of the raw material and the product are hydrolyzed, and a condensate is produced to reduce the yield of the target product.

In order to obtain an excellent coupling agent, it is essential to complete the reaction sufficiently so that the conversion of the raw material becomes 100%, but in this reaction hydrogen halide is produced as a by-product. Therefore, there is no problem in carrying out the reaction using a dehydrohalogenating agent, if necessary. As these dehydrohalogenating agents, raw material aminosilane compounds,
Basic substances which are inert towards halomethylstyrene and (meth) acrylic acid halide are preferred. Examples of the basic substance include amines such as pyridine, triethylamine and tributylamine. The amount of the amine added is usually 0.8 to 10.0 equivalents with respect to the halomethylstyrene and the (meth) acrylic acid halide.

When carrying out this reaction, in order to prevent the polymerization of vinyl groups, a polymerization inhibitor such as p-benzoquinone,
It is also possible to add t-butylcatechol and the like.

The reaction temperature and reaction time are affected by the starting materials and solvents used, and are not particularly limited. However, the stability of unsaturated bonds of halomethylstyrene and (meth) acrylic acid halide is not preferable at too high temperature. The conditions are usually set in the range of 0 to 120 ° C. so that the reaction is completed in 0.5 to 10 hours.

The reaction method is a conventional method, for example, a mixture of an aminosilane compound, an organic solvent, a dehydrohalogenating agent, and a polymerization inhibitor is heated or cooled to a predetermined temperature with stirring, and halomethylstyrene is added thereto. And (meth) acrylic acid halide are added dropwise. Thereafter, if necessary, the hydrogen halide salt, the organic solvent, the excess dehydrohalogenating agent and the like can be removed by filtration or distillation. Halomethylstyrene and (meth)
Either of the acrylic acid halides can be reacted with the aminosilane compound first, but generally, the less reactive halomethylstyrene is reacted with the aminosilane compound first, and then the higher reactivity ( The method of reacting a (meth) acrylic acid halide is advantageous.

The silane coupling agent of the present invention comprising the obtained monoamine compound is (a) a silylalkyl group having a silicon atom substituted with a hydrolyzable group derived from a monoamino-silane compound as a starting material, and a halo as a starting material. It has a (b) vinylbenzyl group derived from methylstyrene and a (c) (meth) acryloyl group derived from a (meth) acrylic acid halide as a starting material, each of which is a monoamino starting material. A monoamine compound in which one nitrogen atom derived from the amino group in the silane compound is substituted.

The silane coupling agent of the present invention comprising a polyamine compound is (a) a silylalkyl group having a hydrolyzable group substituted on a silicon atom derived from a polyamino-silane compound as a starting material, and a halomethyl starting material. Vinylbenzyl group (b) derived from styrene and (c) (meth) derived from (meth) acrylic acid halide as a starting material
A plurality of nitrogens having an acryloyl group and a hydrogen group (d) derived from an amino group in the starting polyamino-silane compound, which are derived from a plurality of amino groups in the starting polyamino-silane compound. Is replaced by an atom,
The number of the substituted groups (a), (b), (c), (d) is n.
When displayed as _a , n _b , n _c , and n _d , respectively, n _a ≧
It is a polyamine compound in which 1, n _b ≧ 1, n _c = 1 and n _d ≧ 0.

The silane coupling agent of the present invention may be an acid salt of the above monoamine compound or polyamine compound. The acid salt is a salt of an organic acid or an inorganic acid, and the organic acid salt may be a salt of any acid such as acetic acid, an aliphatic acid such as propionic acid, an aromatic acid such as benzoic acid, or the like. The acid salt may be a salt of any acid such as hydrochloric acid, sulfuric acid, nitric acid or phosphoric acid. The acid salt can be easily prepared, for example, by neutralizing a monoamine compound or a polyamine compound with a corresponding acid.

The silane coupling agent of the present invention itself is excellent in heat resistance and can give a laminate excellent in heat resistance when the glass fiber product which is a reinforcing material is surface-treated as described later.

The silane coupling agent of the present invention is
It is also possible to use it by mixing with a known silane coupling agent. Known silane coupling agents include, in addition to the above aminosilane compounds, epoxysilanes such as 3-glycidoxypropyltrimethoxysilane,
Acrylic silanes such as 3-methacryloxypropyltrimethoxysilane, chlorosilanes such as 3-chloropropyltrimethoxysilane, mercaptosilanes such as 3-mercaptopropyltrimethoxysilane, vinylsilanes such as vinyltrimethoxysilane Kind and the like.

Next, a method of treating a glass fiber product, which is a reinforcing material of a composite material, with this silane compound to obtain a glass fiber product for laminated plate will be described. Examples of the glass fiber product include conventionally known glass fibers such as alkali glass, non-alkali glass, low-dielectric glass, high-elasticity glass, and E-glass for electrical use. Examples include woven glass mats, glass paper, yarn-woven glass cloth, and glass tape. The glass fiber product in the present invention is to be broadly construed, and includes mica products. As the mica product, for example, a soft laminated mica sheet obtained by making thin pieces into paper, or a baked product thereof can be mentioned.

The glass fiber product (reinforcing material) is treated with this silane compound by using a treatment liquid prepared by diluting the glass fiber product with a suitable solvent. Water as a solvent or 0.5 to
Examples thereof include a 5.0 wt% acetic acid aqueous solution, a 5-99% hydrous alcoholic solution, and a hydrous alcoholic solution containing acetic acid. Further, an emulsifier such as polyoxyethylene higher alcohol ether, polyoxyethylene alkylphenyl ether, polyoxyethylene sorbitan fatty acid ester may be added to these solvents. Furthermore, a dye, a pigment, an antistatic agent, a lubricant, etc. can be added to the treatment liquid, if necessary. The concentration of the silane compound in the solvent is 0.1 to 5.0% by weight, preferably 0.2 to 1.0% by weight.

The treatment of the reinforcing material with the treatment liquid may be carried out by immersing the reinforcing material in the treatment liquid. In some cases, the solution holding ratio of the treatment liquid in the reinforcing material is made constant by using a squeeze roll or the like. Alternatively, the treatment liquid may be spray-coated on a mica sheet or the like. After this treatment, the solvent is removed by drying at 60 to 150 ° C., and at the same time, the reinforcing material reacts with the silanol group of the silane compound.

The amount of the surface treatment agent of the present invention attached to the glass fiber product is 0.001% to 0.4% by weight, preferably 0.01% to 0.3% by weight.

Since the glass fiber product for laminated plate thus obtained is treated with a silane coupling agent having heat resistance, when a laminated plate is produced by using an unsaturated polyester resin or the like as a matrix resin, Excellent heat resistance can be imparted to this laminate.

[0033]

EXAMPLES In order to describe the present invention more specifically, the following examples are given, but the present invention is not limited to these examples. All parts in the examples represent parts by weight.

Example 1 A four-necked flask equipped with a reflux condenser, a thermometer, a dropping funnel and a stirrer was charged with 150 parts of N- (2-aminoethyl) aminopropyltrimethoxysilane and 253 parts of toluene. Under a nitrogen blanket, at 65 ° C with stirring, 103 parts of chloromethylstyrene was added dropwise over 1 hour, and then at 65 ° C
And reacted for 5 hours.

Next, when 130 parts of sodium methylate (28%, methanol solution) was added dropwise over 30 minutes, white crystals, which are considered to be sodium chloride, were precipitated. After cooling to room temperature, the crystals were filtered off, and methanol and toluene were removed by a rotary evaporator to obtain an intermediate reaction product A. From the results of chlorine analysis, it was found that the intermediate reaction product A had 98% or more of chloromethylstyrene reacted.

110 parts of the intermediate reaction product A and 144 parts of toluene were charged into a four-necked flask equipped with a reflux condenser, a thermometer, a dropping funnel, and a stirrer, and 34 parts of methacrylic acid chloride (methacryloyl chloride) was charged under a nitrogen blanket. The mixture was added dropwise over 30 minutes while cooling with ice, then, the mixture was heated to 40 ° C. for 2 hours under ice cooling and reacted for 3 hours.

Infrared absorption spectrum and nuclear magnetic resonance spectrum of the liquid obtained by removing toluene from the obtained reaction liquid by a rotary evaporator were measured. The results are shown in Table 1. From the above measurement results, it was found that the obtained compound had the following average structure.

[0038]

[Chemical 1]

Example 2 The same apparatus as in Example 1 was charged with 125 parts of 3-aminopropyltriethoxysilane, 286 parts of triethylamine and 389 parts of toluene, and the mixture was stirred under a nitrogen blanket while stirring.
86 parts of chloromethylstyrene was added dropwise at 5 ° C over 1 hour,
Further, the reaction was carried out at 65 ° C. for 20 hours.

Next, 59 parts of methacrylic acid chloride (methacryloyl chloride) was added dropwise over 30 minutes while cooling with ice under a nitrogen blanket, and then 40 minutes under cooling with ice for 2 hours.
The temperature was raised to ℃ and reacted for 3 hours.

From the resulting reaction solution, triethylamine hydrochloride was removed by filtration, and the liquid obtained by removing triethylamine and toluene from the filtrate with a rotary evaporator was subjected to infrared absorption spectrum and nuclear magnetic resonance spectrum measurement. The results are shown in Table 1. From the above measurement results, it was found that the obtained compound had the following average structure.

[0042]

[Chemical 2]

Example 3 The same apparatus as in Example 1 was charged with 250 parts of N, N'-bis (trimethoxysilylpropyl) ethylenediamine, 329 parts of triethylamine and 713 parts of toluene, and the mixture was stirred at 65 ° C. under a nitrogen blanket. Then, 99 parts of chloromethylstyrene was added dropwise over 1 hour, and the mixture was further reacted at 65 ° C. for 20 hours.

Next, 59 parts of methacrylic acid chloride (methacryloyl chloride) was added dropwise over 30 minutes while cooling with ice under a nitrogen blanket, and then 40 hours under cooling with ice for 2 hours.
The temperature was raised to ℃ and reacted for 3 hours.

From the resulting reaction solution, triethylamine hydrochloride was removed by filtration, and the liquid obtained by removing triethylamine and toluene from the filtrate with a rotary evaporator was subjected to infrared absorption spectrum and nuclear magnetic resonance spectrum measurement. The results are shown in Table 1. From the above measurement results, it was found that the obtained compound had the following average structure.

[0046]

[Chemical 3]

[0047]

[Table 1]

Example 4 The silane compound of Example 1 was dissolved in 1.0% by weight of distilled water containing 2.0% by weight of acetic acid. Glass cloth (WEA-18W, manufactured by Nitto Boseki Co., Ltd.) was dipped in this solution and squeezed with a squeeze roll to a pickup amount of 30%.
This was dried at 110 ° C. for 5 minutes. The amount of the silane compound attached to the glass cloth was 0.07% by weight.

On the other hand, 100 parts by weight of unsaturated polyester resin, 40 parts by weight of styrene monomer and 1 part by weight of cumene hydroperoxide were mixed to prepare a varnish. Four glass papers (EPM-4050, manufactured by Nippon Vilene Co., Ltd.) were sandwiched between two glass cloths treated with the silane compound, and the above varnish was impregnated. This product was further sandwiched between two copper foils having a thickness of 35 μm, degassed for 2 minutes, and then heated at 150 ° C. for 1 hour to obtain a 1.6 mm laminated plate.

Examples 5-6 Example 4 was repeated except that the silane compound of Example 1 was replaced with the silane compounds of Examples 2 and 3, respectively.
The glass cloth was treated in the same manner as in. The amount of silane compound attached to glass cloth is 0.07% by weight.
Met. Next, in the same manner as in Example 4, 1.6 mm each
The laminated board of was produced.

Comparative Example 1 In Example 4, instead of the silane compound of Example 1, γ
-Using methacryloxypropyltrimethoxysilane, this was added to distilled water containing 0.1% by weight of acetic acid,
The glass cloth was treated in the same manner as in Example 4 except that the glass cloth was dissolved to a concentration of 0.4%. The amount of the silane compound attached to the glass cloth was 0.08% by weight.
Next, in the same manner as in Example 4, a 1.6 mm laminated plate was produced.

Comparative Example 2 In Example 4, the silane compound of Example 1 was replaced with N.
(Vinylbenzyl) -β-aminoethyl-γ-aminopropyltrimethoxysilane was used, and this was dissolved in distilled water containing 2.0% by weight of acetic acid to a concentration of 1.0%. The glass cloth was treated in the same manner as in Example 4. The amount of the silane compound attached to the glass cloth was 0.07% by weight. Next, in the same manner as in Example 4, a 1.6 mm laminated plate was produced.

Solubility Test The silane compounds of Examples 1 to 3 and the silane compounds used in Comparative Examples 1 to 2 were subjected to solubility tests in an aqueous acetic acid solution. That is, 10 g of the silane compound was added to a solution of 10 g of acetic acid dissolved in 1000 g of water, and the solubility at room temperature was observed and evaluated according to the following criteria. ◯: Transparent Δ: Slightly cloudy ×: Cloudy As a result, the silane compounds of Examples 1 to 3 and Comparative Example 1
The silane compound used in Example 1 was evaluated as ◯ (transparent) and was excellent in solubility, but the silane compound used in Comparative Example 2 was evaluated as Δ (slightly cloudy) and was inferior in solubility.

Performance Test The solder heat resistance, the results of the measling characteristic test performed on the laminates obtained by etching the laminates produced in Examples 4 to 6 and Comparatives 1 to 2 to remove the copper foil, and the results of the resin tests. The impregnating property is shown in Table 2. The test method is as follows. (1) Solder Heat Resistance Test The laminated plate was boiled in boiling water for 1 hour, 2 hours, and 3 hours, and then immersed in a solder bath at 260 ° C. for 20 seconds, respectively, and checked for blisters. ○: No blistering ×: Blistering (2) Measing ring characteristic test A soldering iron with a diameter of 2 mm heated to 250 ° C, 270 ° C, and 300 ° C was pressed against the laminated plate for 10 seconds under a load of 100 g, and the measles were measured. The presence or absence of a ring was checked. ◯: No measling ring ×: With measling ring (3) Resin impregnating ability (a) During the production of the laminated plate, the quality of impregnating ability of the unsaturated polyester resin varnish into the glass cloth was visually observed. ⊚: Very good O: Good Δ: Normal ×: Poor (b) The appearance of the laminate was visually observed. ⊚: Very transparent. ◯: Almost transparent. Δ: The weft of the cloth is slightly whitened. X: The warp and weft of the cloth are whitened.

The results are summarized in Table 2. Table 2 Examples Comparative Example 4 5 6 12 Solder heat resistance 1 hour boiling ○ ○ ○ ○ ○ 2 hours boiling ○ ○ ○ × ○ 3 hours boiling ○ ○ ○ × × Measling 250 ° C ○ ○ ○ × ○ Characteristics 270 ° C ○ ○ ○ × × 300 ° C ○ △ × × × Resin impregnation (a) Treated glass ◎ ◎ ◎ ◎ ○ △ Cross (b) Laminated plate ◎ ◎ ◎ ○ × From Table 2, the silane coupling agent of the present invention is used. The thus obtained laminates of Examples 4 to 6 gave satisfactory results in all of solder heat resistance, measling characteristics and resin impregnability. On the other hand, the laminated plates of Comparative Examples 1 and 2 were inferior to the laminated plates of Examples 4 to 6 in all of these characteristics.

[0056]

The silane coupling agent of the present invention is excellent in workability because it is easily dissolved in a solution such as an acetic acid aqueous solution. Further, the composite material using the glass fiber treated with the silane coupling agent of the present invention is excellent in solder heat resistance. Therefore, it becomes possible to provide a printed circuit board that meets the requirements of the surface mounting technology. Further, when the silane coupling agent of the present invention is used, the glass fiber product as a reinforcing material and the matrix resin secure a strong bond even at high temperature. Therefore, in a composite material composed of the both, for example, a printed circuit board, it is possible to prevent the measling from separating the reinforcing material from the matrix resin. Further, the glass fiber product treated with the silane coupling agent of the present invention has an excellent impregnation property with a resin, so that the workability is improved.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification number Internal reference number FI Technical display location C03C 25/02 N 7821-4G C08J 5/08 7188-4F C08K 9/06 KCQ 7167-4J D06M 13 / 513 15/51 H05K 1/03 G 7011-4E (72) Inventor Toshiya Sawai 10-3, Otosetsu-cho, Kanazawa-ku, Yokohama-shi, Kanagawa (72) Innovator Norimasa Otake 10-2 Otsushen-cho, Kanazawa-ku, Yokohama-shi, Kanagawa ( 72) Inventor Hideaki Kakiuchi 358 No. 358 Yonejima, Showa Town, Kita-Katsushika-gun, Saitama Prefecture

Claims (3)

[Claims] 1. A group having one nitrogen atom in the molecule, each of which is represented by the following formulas (a), (b) and (c):
A silane coupling agent, wherein each of the silane coupling agents is a monoamine compound substituted with one nitrogen atom or a salt thereof. (A) Silylalkyl group having a silicon atom substituted with a hydrolyzable group (b) Vinylbenzyl group (c) (meth) acryloyl group 2. A compound having a plurality of nitrogen atoms linked by a divalent organic group in the molecule, the following (a), (b):
The groups represented by (c) and (d) are substituted with the plurality of nitrogen atoms, and the substituted groups (a), (b),
When the numbers of (c) and (d) are represented as n _a , n _b , n _c , and n _d , respectively, n _a ≧ 1, n _b ≧ 1, n _c ≧ 1, n _d
A silane coupling agent comprising a polyamine compound of ≧ 0 or a salt thereof. (A) Silylalkyl group in which a hydrolyzable group is substituted on a silicon atom (b) Vinylbenzyl group (c) (Meth) acryloyl group (d) Hydrogen group 3. A glass fiber product for a laminate, which is treated with the silane coupling agent according to claim 1.