JP6071806B2 - Azole silane compound, synthesis method of the compound and use thereof - Google Patents

Description

  The present invention relates to a novel azolesilane compound.

  The silane coupling agent uses a substance composed of an organic substance and silicon as components. This substance has different types of functional groups in the molecule, and functions as an intermediary between organic materials and inorganic materials that are not familiar to each other. Therefore, it is an indispensable drug for the development and production of composite materials.

  Patent Document 1 discloses a nitrogen-containing heterocyclic ring of an azole compound such as imidazole, benzimidazole, or triazole, a trimethoxysilyl group, a trimethoxysilyl group, or the like as a component of a silane coupling agent used when bonding glass or metal and rubber. Various substances having a structure in which a silyl group such as an ethoxysilyl group is bonded via an organic group including a urethane bond, a thiourethane bond, a urea bond, and the like have been proposed.

JP 2002-363189 A

  An object of the present invention is to provide a novel azole silane compound, a synthesis method thereof, and a silane coupling agent containing the azole silane compound as a component.

  As a result of intensive studies to solve the above-mentioned problems, the inventors of the present invention can synthesize a novel azolesilane compound not described in the literature by reacting an azole compound with an isocyanatopropylsilane compound. And the present invention has been completed.

  That is, the first invention is an azolesilane compound represented by the chemical formula (I).

  A second invention is a method for synthesizing an azolesilane compound according to the first invention, characterized by reacting an azole compound represented by the chemical formula (II) with an isocyanatopropylsilane compound represented by the chemical formula (III). .

（式中、Ｒは前記と同様である。）

(In the formula, R is the same as described above.)

A third invention is a silane coupling agent characterized by comprising the azole silane compound of the first invention as a component.

  The azole silane compound of the present invention is suitable as a component of a silane coupling agent. In addition, since the azole silane compound used as the component of the silane coupling agent of the present invention is a substance having an azole ring together with an alkoxysilyl group, the epoxy resin has a function to rust prevent the metal that is characteristic of the azole compound. It is expected to exhibit the function of curing urethane resin.

Hereinafter, the present invention will be described in detail.
The azolesilane compound of the present invention is represented by the above chemical formula (I),
2,2'-dithiobis {1- [3- (trimethoxysilyl) propylcarbamoyl] -1H-imidazole},
2,2'-dithiobis {1- [3- (triethoxysilyl) propylcarbamoyl] -1H-imidazole},
2,2'-dithiobis {1- [3- (trimethoxysilyl) propylcarbamoyl] -1H-benzimidazole},
2,2'-dithiobis {1- [3- (triethoxysilyl) propylcarbamoyl] -1H-benzimidazole},
2,2'-dithiobis {5-amino-1- [3- (trimethoxysilyl) propylcarbamoyl] -1H-benzimidazole},
2,2'-dithiobis {5-amino-1- [3- (triethoxysilyl) propylcarbamoyl] -1H-benzimidazole},
3,3′-dithiobis {1- [3- (trimethoxysilyl) propylcarbamoyl] -1H-1,2,4-triazole},
3,3′-dithiobis {1- [3- (triethoxysilyl) propylcarbamoyl] -1H-1,2,4-triazole},
3,3′-dithiobis {5-amino-1- [3- (trimethoxysilyl) propylcarbamoyl] -1H-1,2,4-triazole},
3,3′-dithiobis {5-amino-1- [3- (triethoxysilyl) propylcarbamoyl] -1H-1,2,4-triazole},
4,4′-dithiobis {1- [3- (trimethoxysilyl) propylcarbamoyl] -1H-1,2,3-triazole},
4,4'-dithiobis {1- [3- (triethoxysilyl) propylcarbamoyl] -1H-1,2,3-triazole},
5,5'-dithiobis {1- [3- (trimethoxysilyl) propylcarbamoyl] -1H-tetrazole} and 5,5'-dithiobis {1- [3- (triethoxysilyl) propylcarbamoyl] -1H-tetrazole }.

  The azole silane compound of the present invention is produced in a generally high yield by reacting the corresponding precursor dithiodiazole compound and isocyanatopropyl silane compound in an appropriate amount of reaction solvent at an appropriate reaction temperature and reaction time. Although synthesized, an example in which the precursor is 2,2′-dithiodi (1H-imidazole) is shown in Reaction Scheme (A).

（式中、Ｒは前記と同様である。）

(In the formula, R is the same as described above.)

The azole compound that is the precursor of the azole silane compound of the present invention is
2,2'-dithiodi (1H-imidazole),
2,2'-dithiodi (1H-benzimidazole),
2,2'-dithiobis (5-amino-1H-benzimidazole),
3,3′-dithiodi (1H-1,2,4-triazole),
3,3′-dithiobis (5-amino-1H-1,2,4-triazole),
4,4'-dithiodi (1H-1,2,3-triazole) and 5,5'-dithiodi (1H-tetrazole).

The isocyanatopropylsilane compound is
3-isocyanatopropyltrimethoxysilane and 3-isocyanatopropyltriethoxysilane.

The reaction solvent is not particularly limited as long as it is an inert solvent with respect to the azole compound and the isocyanatopropylsilane compound. For example, hydrocarbon solvents such as pentane, hexane, heptane, toluene, xylene;
Ether solvents such as diethyl ether, tetrahydrofuran, dioxane, cyclopentyl methyl ether;
Ester solvents such as ethyl acetate and butyl acetate;
Amide solvents such as formamide, dimethylformamide, dimethylacetamide, pyrrolidone, N-methylpyrrolidone;
Examples thereof include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, and dimethyl sulfoxide.

The reaction of the azole compound and the isocyanatopropylsilane compound according to the present invention proceeds stoichiometrically as illustrated in the above reaction scheme (A), but isocyanate relative to the amount of azole compound used (charged amount). The amount of natopropylsilane compound used (the amount charged) is 1.6 to 2.4 moles in consideration of factors such as reaction temperature and reaction time as well as the types of raw materials and reaction solvents used and reaction scale. It is preferable that the ratio is within an appropriate range.
If the amount of the isocyanatopropylsilane compound charged is more than 2.4 times mol, the compound may be polymerized and gelled, and if less than 0.8 times mol, the purity of the product is lowered. Or the product separation operation becomes complicated.

  The reaction temperature is not particularly limited as long as it is a temperature range in which the nitrogen in the ring (—NH—) of the azole compound and the isocyanato group (—NCO) of the isocyanatopropylsilane compound react, but a range of 0 to 100 ° C. Is preferable, and the range of 5-60 degreeC is more preferable.

  Although the said reaction time is suitably determined according to the set reaction temperature, the range of 30 minutes-20 hours is preferable, and the range of 1-8 hours is more preferable.

In using the silane coupling agent having the azole silane compound of the present invention as a component, the same surface treatment method as that of the conventional silane coupling agent can be employed.
As this surface treatment method, for example, (a) a method of spray-coating a treatment liquid obtained by diluting an appropriate amount of a silane coupling agent with an organic solvent, (b) the silane coupling agent with a water-organic solvent A method of spray-coating a diluted treatment liquid on a substrate, (c) a method of immersing the substrate in a treatment solution obtained by diluting the silane coupling agent with an organic solvent, and (d) a water-organic solvent containing the silane coupling agent. The method of immersing a base material in the process liquid diluted by this is mentioned.

Examples of the organic solvent include hydrocarbon solvents such as benzene, toluene, xylene, heptane, hexane, cyclohexane, and n-octane;
Halogenated hydrocarbon solvents such as dichloromethane, dichloroethane, carbon tetrachloride, chloroform, chlorobenzene, dichlorobenzene, trichlorobenzene;
Ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone;
Ether solvents such as diethyl ether, tetrahydrofuran, dioxane, ethylene glycol monomethyl ether (methyl cellosolve), ethylene glycol monoethyl ether (ethyl cellosolve), ethylene glycol monobutyl ether (butyl cellosolve), diethylene glycol monobutyl ether;
Examples include alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, n-butyl alcohol, sec-butyl alcohol, tert-butyl alcohol, ethylene glycol, diethylene glycol, and propylene glycol.

  Examples of the substrate to be treated with the silane coupling agent having the azole silane compound of the present invention as a component include, for example, silica, alumina, aluminosilicate, aluminum hydroxide, magnesium carbonate, magnesium oxide, calcium carbonate, and zinc oxide. Granular materials such as zinc carbonate, iron oxide, titanium dioxide, mica, fibers such as glass fiber, nylon fiber, carbon fiber, etc., glass plate, aluminum plate, copper plate, copper foil, copper plating film, steel plate, iron plate, Examples include stainless steel plates.

By applying such a surface treatment to the base material, the lipophilicity of the surface of the base material is increased, and the affinity (adhesiveness, adhesion) to the resin or the like can be improved.
In addition, in order to raise the effect by this process, you may heat-process the surface-treated base material.

EXAMPLES Hereinafter, although an Example (synthesis test, evaluation test) demonstrates this invention concretely, this invention is not limited to these.
The azole compound and isocyanatopropylsilane compound used in the synthesis test are shown below.

[Azole compounds]
-2,2'-dithiodi (1H-imidazole): synthesized according to the method described in the pamphlet of International Publication No. 2012/031183-2,2'-dithiodi (1H-benzimidazole): JP-A-2013-14752 3,3'-dithiodi (1H-1,2,4-triazole): synthesized according to the method described in International Publication No. 2012/031183. 3,3'-dithiobis (5- Amino-1H-1,2,4-triazole): Same as above. 4,4′-dithiodi (1H-1,2,3-triazole): same as above.

[Isocyanatopropylsilane compound]
・ 3-isocyanatopropyltrimethoxysilane: manufactured by Momentive Performance Materials Japan ・ 3-isocyanatopropyltriethoxysilane: manufactured by Shin-Etsu Chemical Co., Ltd.

A test of adhesiveness between copper and resin, which was performed to evaluate the azole silane compound of the present invention as a component of the silane coupling agent, is shown below.
[Adhesion test]
(1) Test piece Electrolytic copper foil (thickness: 18 μm) was used as a test piece.
(2) Processing of test piece It performed according to the following processes ac.
a. Acid clean / 1 minute (room temperature), water wash b. Acid cleaning / 1 minute (room temperature), water washing, drying / 1 minute (100 ° C)
c. Immersion in copper surface treatment solution / 1 minute (room temperature), water washing, drying / 1 minute (100 ° C.)
(3) Bonding of test piece and resin A glass cloth epoxy resin-impregnated prepreg (FR-4 grade) was laminated and pressed on the S surface of the treated test piece, and the test piece and the resin were bonded.
(4) Evaluation of Adhesiveness According to “JIS C6418”, a test piece having a width of 10 mm was prepared and subjected to pressure cooker treatment (121 ° C./humidity 100% / 100 hours), and then the peel strength of the copper foil was measured.

[Example 1]
<Synthesis of 2,2'-dithiobis {1- [3- (trimethoxysilyl) propylcarbamoyl] -1H-imidazole}
2.0 g (10 mmol) of 2,2′-dithiodi (1H-imidazole) was added to 45 g of dehydrated dimethylformamide and dissolved by stirring at room temperature, and 4.1 g of 3-isocyanatopropyltrimethoxysilane ( 20 mmol) was added dropwise.
After the exotherm had subsided, the mixture was stirred at 40 ° C. for 6 hours, and the reaction solution was concentrated under reduced pressure to obtain 6.5 g (10 mmol, yield 100%) of a brown liquid.

The ¹ H-NMR spectrum data of the obtained liquid was as follows.
・¹ H-NMR (DMSO-d ₆ ) δ: 8.72 (t, 2H), 7.79 (d,
2H), 6.97 (d, 2H), 3.48 (s, 18H), 3.3-3.2 (m, 4H), 1.6-1.5 (m, 4H), 0.65 (t, 4H).

Further, the IR spectrum data of this liquid was as shown in the chart of FIG.
From these spectral data, the obtained liquid was identified as the title azolesilane compound represented by the chemical formula (I-1).

[Example 2]
<2,2′-dithiobis {1- [3- (triethoxysilyl) propylcarbamoyl] -1H-imidazole}
Synthesis>
1.0 g (5 mmol) of 2,2′-dithiodi (1H-imidazole) was added to 26 g of dehydrated dimethylformamide and dissolved by stirring at room temperature, and 2.5 g of 3-isocyanatopropyltriethoxysilane ( 10 mmol) was added dropwise.
After the exotherm had subsided, the mixture was stirred at 40 ° C. for 6 hours, and the reaction solution was concentrated under reduced pressure to obtain 3.5 g (5 mmol, yield 100%) of a brown liquid.

The ¹ H-NMR spectrum data of the obtained liquid was as follows.
・¹ H-NMR (DMSO-d ₆ ) δ: 8.75 (t, 2H), 7.79 (d,
2H), 6.98 (d, 2H), 3.77 (q, 12H), 3.3-3.2 (m, 4H), 1.7-1.5 (m, 4H), 1.15 (t, 18H), 0.62 (t,
4H).

Further, the IR spectrum data of this liquid was as shown in the chart of FIG.
From these spectral data, the obtained liquid was identified as the title azole silane compound represented by the chemical formula (I-2).

[Example 3]
<2,2′-dithiobis {1- [3- (trimethoxysilyl) propylcarbamoyl] -1H-benzimidazole}
Synthesis>
2.5 g (8.4 mmol) of 2,2'-dithiodi (1H-benzimidazole) was added to 16 g of dehydrated dimethylformamide and dissolved by stirring at room temperature. 3-isocyanatopropyltrimethoxysilane 3 0.5 g (17 mmol) was added dropwise.
After the exotherm had subsided, the mixture was stirred at 40 ° C. for 4 hours, and the reaction solution was concentrated under reduced pressure to obtain 6.1 g (8.4 mmol, yield 100%) of a brown liquid.

The ¹ H-NMR spectrum data of the obtained liquid was as follows.
¹ H-NMR (DMSO-d ₆ ) δ: 8.55 (s, 2H), 8.07 (d,
2H), 7.72 (d, 2H), 7.4-7.2 (m, 4H), 3.49 (s, 18H), 3.4-3.2 (m, 4H), 1.8-1.6 (m, 4H), 0.68 (t, 4H) .

Further, the IR spectrum data of this liquid was as shown in the chart of FIG.
From these spectral data, the obtained liquid was identified as the title azolesilane compound represented by the chemical formula (I-3).

[Example 4]
<2,2′-dithiobis {1- [3- (triethoxysilyl) propylcarbamoyl] -1H-benzimidazole}
Synthesis>
1.0 g (3.3 mmol) of 2,2′-dithiodi (1H-benzimidazole) is added to 10 g of dehydrated dimethylformamide and dissolved by stirring at room temperature. 3-isocyanatopropyltriethoxysilane 1 0.7 g (6.8 mmol) was added dropwise.
After the exotherm had subsided, the mixture was stirred at 40 ° C. for 4 hours, and the reaction solution was concentrated under reduced pressure to obtain 2.6 g (3.3 mmol, yield 100%) of a brown liquid.

The ¹ H-NMR spectrum data of the obtained liquid was as follows.
・¹ H-NMR (DMSO-d ₆ ) δ: 8.56 (s, 2H), 8.08 (d,
2H), 8.73 (d, 2H), 7.5-7.3 (m, 4H), 3.77 (q, 12H), 3.4-3.2 (m, 4H), 1.8-1.6 (m, 4H),
1.16 (t, 18H), 0.67 (t, 4H).

Further, the IR spectrum data of this liquid was as shown in the chart of FIG.
From these spectral data, the obtained liquid was identified as the title azolesilane compound represented by the chemical formula (I-4).

[Example 5]
<Synthesis of 3,3′-dithiobis {1- [3- (trimethoxysilyl) propylcarbamoyl] -1H-1,2,4-triazole}>
4.02 g (20.1 mmol) of 3,3′-dithiodi (1H-1,2,4-triazole) was added to 150 g of dehydrated dimethylformamide and dissolved by stirring at room temperature, and 3-isocyanato was dissolved therein. 9.49 g (46.2 mmol) of propyltrimethoxysilane was added dropwise. Ten minutes later, 0.92 g (9.1 mmol) of triethylamine was added, and the mixture was stirred at 60 ° C. for 8 hours.
The reaction solution was concentrated under reduced pressure to obtain 12.3 g (20.1 mmol, yield 100%) of a pale yellow liquid.

The ¹ H-NMR spectrum data of the obtained liquid was as follows.
・¹ H-NMR (DMSO-d ₆ ) δ: 9.20 (s, 2H),
8.78 (t, 2H), 3.47 (s, 18H), 3.21 (q, 4H), 1.60 (m, 4H), 0.59 (t, 4H).

Further, the IR spectrum data of this liquid was as shown in the chart of FIG.
From these spectral data, the obtained liquid was identified as the title azolesilane compound represented by the chemical formula (I-5).

[Example 6]
<Synthesis of 3,3′-dithiobis {1- [3- (triethoxysilyl) propylcarbamoyl] -1H-1,2,4-triazole}>
1.0 g (5 mmol) of 3,3′-dithiodi (1H-1,2,4-triazole) was added to 24 g of dehydrated dimethylformamide and dissolved by stirring at room temperature. Ethoxysilane 2.5g (10mmol) was dripped. 20 minutes later, 0.2 g (2 mmol) of triethylamine was added, and the mixture was stirred at 40 ° C. for 6 hours. The reaction solution was concentrated under reduced pressure to obtain 3.7 g of crude crystals. This was recrystallized from ethanol to obtain 2.6 g (3.7 mmol, yield 75.0%) of white crystals.

The melting point and ¹ H-NMR spectrum data of the obtained crystal were as follows.
Melting point: 91-93 ° C
・¹ H-NMR (DMSO-d ₆ ) δ: 9.20 (s, 2H), 8.79 (t,
2H), 3.75 (q, 12H), 3.3-3.2 (m, 4H), 1.6-1.5 (m, 4H), 1.16 (t, 18H), 0.57 (t, 4H).

The IR spectrum data of this crystal was as shown in the chart in FIG.
From these spectral data, the obtained crystal was identified as the title azole silane compound represented by the chemical formula (I-6).

[Example 7]
<Synthesis of 3,3′-dithiobis {5-amino-1- [3- (trimethoxysilyl) propylcarbamoyl] -1H-1,2,4-triazole}>
2.00 g (8.7 mmol) of 3,3′-dithiobis (5-amino-1H-1,2,4-triazole) was added to 45 g of dehydrated dimethylformamide and dissolved by stirring at room temperature. -3.56 g (17.3 mmol) of isocyanatotrimethoxypropylsilane was added dropwise. Five minutes later, 0.3 g (3 mmol) of triethylamine was added, and the mixture was stirred at 55 ° C. for 5 hours.
The reaction solution was concentrated under reduced pressure, and 12.8 g of the resulting concentrate was recrystallized twice from dehydrated methanol and dried under reduced pressure to obtain 3.65 g (5.7 mmol, yield 65.5%) of white crystals. Obtained.

The melting point and ¹ H-NMR spectrum data of the obtained crystal were as follows.
Melting point: 143-144.3 ° C
^-1 H-NMR (CDCl ₃ ) δ: 8.22 (t, 2H),
7.43 (br.s, 4H), 3.47 (s, 18H), 3.15 (q, 4H), 1.57 (quint, 4H), 0.57 (t, 4H).

The IR spectrum data of this crystal was as shown in the chart of FIG.
From these spectral data, the obtained crystal was identified as the title azole silane compound represented by the chemical formula (I-7).

[Example 8]
<Synthesis of 3,3′-dithiobis {5-amino-1- [3- (triethoxysilyl) propylcarbamoyl] -1H-1,2,4-triazole}>
1.0 g (4.3 mmol) of 3,3′-dithiobis (5-amino-1H-1,2,4-triazole) was added to 13 g of dehydrated dimethylformamide and dissolved by stirring at room temperature. -2.1 g (8.6 mmol) of isocyanatopropyltriethoxysilane was added dropwise. 20 minutes later, 0.2 g (2 mmol) of triethylamine was added, and the mixture was stirred at 40 ° C. for 6 hours. The reaction solution was concentrated under reduced pressure to obtain 3.2 g of crude crystals.
The crystals were recrystallized from ethanol to obtain 2.1 g (2.9 mmol, yield 67.4%) of white crystals.

The melting point and ¹ H-NMR spectrum data of the obtained crystal were as follows.
Melting point: 164-165 ° C
^-1 H-NMR (CDCl ₃ ) δ: 8.23 (t, 2H), 7.44 (s,
4H), 3.74 (q, 12H), 3.2-3.1 (m, 4H), 1.6-1.5 (m, 4H), 1.15 (s, 18H), 0.53 (t, 4H)

The IR spectrum data of this crystal was as shown in the chart of FIG.
From these spectral data, the obtained crystal was identified as the title azole silane compound represented by the chemical formula (I-8).

[Example 9]
<Synthesis of 4,4'-dithiobis {1- [3- (trimethoxysilyl) propylcarbamoyl] -1H-1,2,3-triazole}>
8.67 g (43.3 mmol) of 4,4′-dithiodi (1H-1,2,3-triazole) was added to 50 g of dehydrated dimethylformamide and dissolved by stirring at room temperature. 18.7 g (91.1 mmol) of natopropyltrimethoxysilane was added dropwise, 20 minutes later, 1.84 g (18.2 mmol) of triethylamine was added, and the mixture was stirred at room temperature for 15 hours.
After the reaction solution was concentrated under reduced pressure, the liquid concentrate was washed with 130 mL of hexane and dried under reduced pressure to obtain 26.0 g (42.6 mmol, yield 98.3%) of a brown liquid.

The ¹ H-NMR spectrum data of the obtained liquid was as follows.
¹ H-NMR (CDCl ₃ ) δ: 8.99 (t, 2H),
8.43 (s, 2H), 3.47 (s, 18H), 3.26 (q, 4H), 1.63 (m, 4H), 0.62 (t, 4H).

Further, the IR spectrum data of this liquid was as shown in the chart of FIG.
From these spectral data, the obtained liquid was identified as the title azolesilane compound represented by the chemical formula (I-9).

[Example 10]
<Synthesis of 4,4'-dithiobis {1- [3- (triethoxysilyl) propylcarbamoyl] -1H-1,2,3-triazole}>
1.0 g (5 mmol) of 4,4′-dithiodi (1H-1,2,3-triazole) is added to 10 g of dehydrated dimethylformamide and dissolved by stirring at room temperature, and 3-isocyanatopropyltriethoxysilane is dissolved therein. 2.5 g (10 mmol) was added dropwise. Twenty minutes later, 0.1 g (1 mmol) of triethylamine was added and stirred at 40 ° C. for 8 hours. The reaction solution was concentrated under reduced pressure to obtain 3.5 g (5 mmol, yield 100%) of a brown liquid.

The obtained liquid ¹ H-NMR spectrum data was as follows.
・¹ H-NMR (CDCl ₃ ) δ: 8.99 (t, 2H), 8.45 (s,
2H), 3.75 (q, 12H), 3.4-3.2 (m, 4H), 1.7-1.6 (m, 4H), 1.16 (t, 18H), 0.59 (t, 4H).

Further, the IR spectrum data of this liquid was as shown in the chart of FIG.
From these spectral data, the obtained liquid was identified as the title azolesilane compound represented by the chemical formula (I-10).

[Example 11]
<Preparation and Evaluation of Copper Surface Treatment Solution>
A copper surface treatment solution was prepared using the azole silane compound synthesized in Example 1 as the silane coupling agent component.
That is, 200 g of ethylene glycol monobutyl ether was added to 10 g of this compound, followed by addition of 790 g of water, followed by stirring at room temperature for 2 hours to hydrolyze the methoxysilyl group (—Si (OCH ₃ ) ₃ ) of the azolesilane compound. Thus, a copper surface treatment solution (hereinafter referred to as treatment solution A) having a hydroxysilyl group (—Si (OH) ₃ ) was prepared.
In the same manner, a copper surface treatment solution was prepared using the azole silane compounds synthesized in Examples 2-3, 5, and 7-9 instead of the azole silane compounds synthesized in Example 1. Hereinafter, they are referred to as treatment liquids B, C, D, E, F, and G).
The methoxysilyl group (—Si (OCH ₃ ) ₃ ) or ethoxysilyl group (—Si (O CH ₂ CH ₃ ) ₃ ) of the azolesilane compound in these treatment liquids is replaced with a hydroxysilyl group (—Si (OH). ) It was confirmed that it was hydrolyzed in ₃ ).
A copper surface treatment liquid (hereinafter referred to as treatment liquid H) having the same composition as the treatment liquids A to G was prepared except that no silane coupling agent component was used.

  When these treatment liquids were subjected to an adhesion test, the test results obtained were as shown in Table 1, and the copper surface treatment using the azole silane compound of the present invention as a component of the silane coupling agent. It is recognized that the liquid exhibits the effect of enhancing the adhesion between the copper surface and the prepreg.

2 is an IR spectrum chart of the liquid obtained in Example 1. 4 is an IR spectrum chart of the liquid obtained in Example 2. 4 is an IR spectrum chart of the liquid obtained in Example 3. 6 is an IR spectrum chart of the liquid obtained in Example 4. 6 is an IR spectrum chart of the liquid obtained in Example 5. 7 is an IR spectrum chart of the crystal obtained in Example 6. 7 is an IR spectrum chart of the crystal obtained in Example 7. 7 is an IR spectrum chart of the crystal obtained in Example 8. 10 is an IR spectrum chart of the liquid obtained in Example 9. 6 is an IR spectrum chart of the liquid obtained in Example 10.

  By using the azole silane compound of the present invention as a component, it is possible to provide a silane coupling agent having a function of rust-proofing the metal that is a feature of the azole compound and a function of curing an epoxy resin or a urethane resin. Use in composite materials such as printed wiring boards manufactured by combining different types of materials is expected.

Claims (3)

An azolesilane compound represented by the chemical formula (I).

The method for synthesizing an azolesilane compound according to claim 1, wherein the azole compound represented by the chemical formula (II) is reacted with the isocyanatopropylsilane compound represented by the chemical formula (III).

(In the formula, R is the same as described above.) A silane coupling agent comprising the azole silane compound according to claim 1 as a component.

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