JP6462539B2 - Triazine compound, method for synthesizing the compound and use thereof - Google Patents

Description

  The present invention relates to a novel triazine compound, a method for synthesizing the compound, and an application using the compound.

Polymers such as epoxy resins, phenol resins, and polyester resins are thermosetting and excellent in corrosion resistance and electrical insulation, so in the fields of electronic components and printed circuit boards, adhesives, conductive pastes, It is widely used as a raw material for resist inks, sealing materials, insulating materials, substrate matrix materials, and the like.
However, such a polymer has a function to suppress migration, that is, a function to suppress a phenomenon that a metal constituting a wiring (circuit) or an electrode on an insulating material moves on the insulating material due to a potential difference in a high humidity environment. Therefore, there is a problem that it causes an insulation failure of electronic parts and printed circuit boards.
In addition, further improvement in adhesion between these polymers and a metal material such as copper or an inorganic material such as a glass substrate has been demanded.

Various substances are used as additives for solving such problems. Among them, a substance having a triazine skeleton is said to be effective for suppressing the migration and improving the adhesion with various metals.
For example, Patent Document 1 proposes an epoxy resin composition for semiconductor encapsulation containing a triazine compound having two mercapto groups in one molecule. Patent Document 2 proposes a method for producing a 2-mercapto-S-triazine derivative.
However, the adhesion improving effect derived from these triazine compounds has not been sufficient yet.

JP 2005-132877 A Japanese Patent Publication No. 40-23025

  It is an object of the present invention to provide a triazine compound that exhibits an excellent adhesion improving effect, a method for synthesizing the compound, a resin composition containing the compound expected to be used in various applications, and a surface treatment agent. To do.

As a result of intensive studies to solve the above-mentioned problems, the inventors of the present invention can achieve the intended purpose by obtaining a triazine compound having a mercapto group and an amino group substituted by a specific group. As a result, the present invention has been completed.
That is, the first invention is a triazine compound represented by Structural Formula (II).

（式中、Ｙは互いに同一であっても異なってもよく、水素原子またはＳｉ(ＯＲ^２)_３を表す。Ｒ^１およびＲ^２は互いに同一であっても異なってもよく、水素原子または炭素数１〜６のアルキル基を表す。ｑは互いに同一であっても異なってもよく、０〜１０の整数を表す。）

(In the formula, Y may be the same or different and each represents a hydrogen atom or Si (OR ² ) _3. R ¹ and R ² may be the same or different from each other, and represent a hydrogen atom or a carbon atom. And represents an alkyl group having 1 to 6. q may be the same or different from each other, and represents an integer of 0 to 10.

The second invention is a method for synthesizing the triazine compound represented by the chemical formula (II) of the first invention, characterized by reacting the triazine compound represented by the chemical formula (IV) with sodium hydrosulfide.

（式中、Ｙ、Ｒ^１およびｑは前記と同様である。）

(Wherein, Y, R ¹ and q are the same as above.)

A third invention is a resin composition comprising a triazine compound represented by the chemical formula (II) of the first invention .

A fourth invention is a resin composition for an adhesive or a sealant characterized by containing a triazine compound represented by the chemical formula (II) of the first invention .

5th invention is a resin composition for semiconductor sealing agents characterized by containing the triazine compound shown by Chemical formula (II) of 1st invention .

6th invention is a surface treating agent characterized by containing the triazine compound shown by chemical formula (II) of 1st invention .

A seventh invention is a solder resist ink characterized by containing a triazine compound represented by the chemical formula (II) of the first invention .

An eighth invention is a copper foil characterized in that the surface treatment agent of the sixth invention is applied to the surface.

The ninth invention is a copper-clad laminate characterized by using the resin composition of the third invention.

The tenth invention is an interlayer insulating material characterized by using the resin composition of the third invention.

An eleventh invention is a copper foil with a resin characterized by using the resin composition of the third invention.

A twelfth invention is a prepreg characterized by applying the resin composition of the third invention on the surface of a sheet-like reinforcing base material or impregnating the reinforcing base material.

A thirteenth invention is a printed wiring board characterized in that the surface treating agent of the sixth invention is applied to the surface.

The triazine compound of the present invention is an epoxy resin, phenol resin, polyester resin, acrylic resin, polystyrene resin, epoxy (meth) acrylate resin, polyimide resin, bismaleimide resin, bismaleimide triazine resin, cyanate ester resin, cycloolefin resin, polyphenylene. When used as an additive for polymers such as ether resin, benzoxazine resin, and fluororesin, the triazine compound dissolves or uniformly disperses in the polymer, thereby suppressing the migration of electronic components, printed wiring boards, etc. In addition, it exerts the effect of improving the adhesion between the polymer and the metal materials and inorganic materials such as copper, aluminum, titanium, nickel, tin, iron, zinc, silver, platinum, and gold constituting the electronic component or printed wiring board. Expected to be .
In addition, when the surface treatment agent containing the triazine compound of the present invention is applied to a copper foil and a printed wiring board, copper, aluminum, titanium, nickel, tin, iron, zinc constituting an electronic component or a printed wiring board It is expected to exhibit the effect of improving the adhesion between the metal material such as silver, platinum, and gold and the inorganic material and the polymer.

2 is an IR spectrum chart of the crystal obtained in Example 1. FIG.

Hereinafter, the present invention will be described in detail.
Triazine compounds of the present invention is represented by the above-mentioned chemical formula (II).

As an example of the triazine compound represented by the chemical formula (II),
2-mercapto-4,6-bis (alkoxysilylmethylamino) -1,3,5-triazine,
2-mercapto-4,6-bis [(2-alkoxysilylethyl) amino] -1,3,5-triazine,
2-mercapto-4,6-bis [(3-alkoxysilylpropyl) amino] -1,3,5-triazine,
2-mercapto-4,6-bis [(4-alkoxysilylbutyl) amino] -1,3,5-triazine,
2-mercapto-4,6-bis [(5-alkoxysilylpentyl) amino] -1,3,5-triazine,
2-mercapto-4,6-bis [(6-alkoxysilylhexyl) amino] -1,3,5-triazine,
2-mercapto-4,6-bis [(8-alkoxysilyloctyl) amino] -1,3,5-triazine,
2-mercapto-4,6-bis [(10-alkoxysilyldecyl) amino] -1,3,5-triazine,
Examples include 2-mercapto-4,6-bis [(3-hydroxysilylpropyl) amino] -1,3,5-triazine.
Here, alkoxy refers to methoxy, ethoxy, propoxy, butoxy and the like.

  The triazine compound represented by the chemical formula (II) is synthesized by reacting the triazine compound represented by the chemical formula (IV) with sodium hydrosulfide in an appropriate amount of reaction solvent at an appropriate reaction temperature and reaction time. can do.

As an example of the triazine compound represented by the chemical formula (IV),
2-chloro-4,6-bis (alkoxysilylmethylamino) -1,3,5-triazine,
2-chloro-4,6-bis [(2-alkoxysilylethyl) amino] -1,3,5-triazine,
2-chloro-4,6-bis [(3-alkoxysilylpropyl) amino] -1,3,5-triazine,
2-chloro-4,6-bis [(4-alkoxysilylbutyl) amino] -1,3,5-triazine,
2-chloro-4,6-bis [(5-alkoxysilylpentyl) amino] -1,3,5-triazine,
2-chloro-4,6-bis [(6-alkoxysilylhexyl) amino] -1,3,5-triazine,
2-chloro-4,6-bis [(8-alkoxysilyloctyl) amino] -1,3,5-triazine,
Examples include 2-chloro-4,6-bis [(10-alkoxysilyldecyl) amino] -1,3,5-triazine.
Here, alkoxy refers to methoxy, ethoxy, propoxy, butoxy and the like.

Sodium water sulfate of said relative triazine 1 mole of the compound represented by the formula (IV), typically used in the range of 1.0 to 2.0 mol.

  Examples of the reaction solvent include alcohol solvents such as methanol and ethanol, halogen solvents such as chloroform and dichloromethane, hydrocarbon solvents such as toluene and hexane, ether solvents such as tetrahydrofuran and 1,4-dioxane, and the like. Examples thereof include dimethyl sulfoxide (DMSO).

  About the said reaction temperature, it can set suitably within the range of 10-120 degreeC. The reaction time is appropriately determined according to the set reaction temperature, but is preferably 0.5 to 24 hours, and more preferably 1 to 6 hours.

  After the reaction with the triazine compound represented by the chemical formula (IV) and sodium hydrosulfide, the desired triazine compound can be obtained from the obtained reaction mixture by, for example, crystallization operation or extraction operation. If necessary, the target triazine compound can be further purified by washing with a solvent such as water or activated carbon treatment.

(About resin composition)
The triazine compound represented by the chemical formula (II) is blended with a curing agent and, if necessary, with a curing agent and a curing accelerator (curing catalyst), one or two or more different types in the resin. It can be a composition.

The compounding amount of the triazine compound in the resin composition of the present invention containing the triazine compound represented by the chemical formula (II) (for adhesive, sealant and semiconductor encapsulant) is 100 parts by weight of resin. It is preferable to set it as the ratio of 0.01-150 weight part, and it is more preferable to set it as the ratio of 0.1-50 weight part.
And it is preferable to set it as the ratio of 0.01-300 weight part with respect to 100 weight part of resin, and, as for the compounding quantity of a hardening | curing agent, it is more preferable to set it as the ratio of 0.1-200 weight part.
Moreover, it is preferable to set it as the ratio of 0.01-2 weight part with respect to 100 weight part of resin, and, as for the compounding quantity of a hardening accelerator, it is more preferable to set it as the ratio of 0.1-0.5 weight part.

Examples of the resin include epoxy resin, phenol resin, polyester resin, acrylic resin, polystyrene resin, epoxy (meth) acrylate resin, polyimide resin, bismaleimide resin, bismaleimide triazine resin, cyanate ester resin, cycloolefin resin, Examples thereof include polyphenylene ether resin, benzoxazine resin, and fluorine resin.
Among these resins, an epoxy resin is particularly preferable.

The epoxy resin may be a substance having at least two epoxy groups in the molecule, but may be a mixture of a substance having at least two epoxy groups in the molecule and a substance having one epoxy group in the molecule. There may be.
As an example of such an epoxy resin,
Bisphenol A type epoxy resin, bisphenol F type epoxy resin, novolak type epoxy resin such as phenol novolak type epoxy resin and cresol novolak type epoxy resin, alicyclic epoxy resin, 3 ', 4'-epoxycyclohexylmethyl-3,4- Cyclic alicyclic epoxy resins such as epoxycyclohexanecarboxylate, 1,3,4,6-tetraglycidylglycoluril, 1,3,4,6-tetraglycidyl-3a, 6a-dimethylglycoluril, 1,3,4 Nitrogen-containing cyclic epoxy resins such as 4,6-tetraglycidyl-3a, 6a-diphenylglycoluril, triglycidyl isocyanurate, monoallyl diglycidyl isocyanurate, diallyl monoglycidyl isocyanurate and hydantoin type epoxy resin, Bisphenol A type epoxy resin, aliphatic epoxy resin, glycidyl ether type epoxy resin, bisphenol S type epoxy resin, biphenyl type epoxy resin, dicyclocyclic type epoxy resin, naphthalene type epoxy resin, halogenated epoxy resin, etc., carbon -Epoxy-modified organopolysiloxane compounds by hydrosilylation addition reaction between an organic compound having a carbon double bond and a glycidyl group and a silicon compound having a SiH group (for example, JP 2004-99751 A and JP 2006-282888 A). Epoxy-modified organopolysiloxane compounds disclosed in the publication).
In addition, the epoxy resin here refers to the epoxy compound before hardening.

As an example of the curing agent,
In addition to compounds having phenolic hydroxyl groups, acid anhydrides and amines, mercaptan compounds such as mercaptopropionic acid esters and epoxy resin-terminated mercapto compounds, organic phosphine compounds such as triphenylphosphine, diphenylnaphthylphosphine and diphenylethylphosphine, aromatic Examples thereof include phosphonium salts, aromatic diazonium salts, aromatic iodonium salts, and aromatic selenium salts.

Examples of the compound having a phenolic hydroxyl group include
Bisphenol A, Bisphenol F, Bisphenol S, Tetramethylbisphenol A, Tetramethylbisphenol F, Tetramethylbisphenol S, Tetrachlorobisphenol A, Tetrabromobisphenol A, Dihydroxynaphthalene, Phenol novolac, Cresol novolac, Bisphenol A novolak, Brominated phenol Examples include novolak and resorcinol.

Examples of the acid anhydride include
Methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, hexahydrophthalic anhydride, 5-norbornene-2,3-dicarboxylic acid anhydride, trimellitic anhydride, nadic acid anhydride, highmic acid anhydride, methyl nadic acid anhydride , Methylbicyclo [2.2.1] heptane-2,3-dicarboxylic acid anhydride, bicyclo [2.2.1] heptane-2,3-dicarboxylic acid anhydride, methylnorbornane-2,3-dicarboxylic acid An anhydride etc. are mentioned.

Examples of the amines include
Diethylenediamine, triethylenetetramine, hexamethylenediamine, dimer acid-modified ethylenediamine, 4,4'-diaminodiphenylsulfone, 4,4'-diaminodiphenol ether, 1,8-diazabicyclo [5.4.0] -7- Examples include undecene, and imidazole compounds such as 2-methylimidazole, 2-ethyl-4-methylimidazole, and 2-phenylimidazole.

Examples of the curing accelerator include
1,8-diazabicyclo [5.4.0] -7-undecene, diethylenetriamine, triethylenetetramine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, tris (dimethylaminomethyl) phenol and other amine compounds, 2-methyl Imidazole compounds such as imidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole and 2-heptadecylimidazole, organic phosphine compounds such as tributylphosphine, methyldiphenylphosphine, triphenylphosphine, diphenylphosphine and phenylphosphine, tetrabutyl Phosphonium compounds such as phosphonium bromide, tetrabutylphosphonium diethyl phosphorodithioate, tetraphenylphosphonium tetraphenylborate Salts, tetraphenylboron salts such as 2-methyl-4-methylimidazole tetraphenylborate, N-methylmorpholine tetraphenylborate, aliphatic acid metal salts such as lead acetate, tin octylate, cobalt hexanoate, etc. Can be mentioned.
Some of these substances are also used as the aforementioned curing agent.

In the resin composition of the present invention, if necessary, inorganic silica, crystalline silica, calcium carbonate, magnesium carbonate, alumina, magnesia, clay, talc, calcium silicate, titanium oxide and other inorganic fillers, cellulose, Fiber filler such as glass fiber, boron fiber, carbon fiber, carbon black, graphite, carbon nanotube, fullerene, iron oxide, gold, silver, aluminum powder, iron powder, nickel, copper, zinc, chromium, solder, nano size Metallic crystals, conductive fillers such as intermetallic compounds, aliphatic polyols such as ethylene glycol and propylene glycol, carbon dioxide generation inhibitors such as aliphatic or aromatic carboxylic acid compounds and phenol compounds, and polyalkylene glycols Flexibility imparting agent, antioxidant, plasticizer, lubricant, coupling agent such as silane, Surface treatment agents for machine fillers, flame retardants, antistatic agents, coloring agents, leveling agents, ion trapping agents, slidability improving agents, various rubbers, impact resistance improving agents, thixotropic agents, surfactants, surface Additives such as a tension reducing agent, an antifoaming agent, an anti-settling agent, a light diffusing agent, an ultraviolet absorber, an antioxidant, a release agent, and a fluorescent agent can be blended.
In addition, phenol resins, polyester resins, acrylic resins, polystyrene resins, polyurethane resins, polyether resins, melamine resins, acrylic-modified epoxy resins, urethane-modified epoxies are used to improve the properties of main component resins. A resin different from the main component resin selected from a resin, a rubber-modified epoxy resin, an alkyd-modified epoxy resin, and the like can be blended.

  Further, the resin composition of the present invention includes an organic solvent such as toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, butyl glycidyl for the purpose of making the resin composition a solvent (solution) and adjusting the viscosity. Reactive diluents such as ether, N, N'-diglycidyl-o-toluidine, phenylglycidyl ether, styrene oxide, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, dioctyl phthalate Non-reactive diluents such as dibutyl phthalate, dioctyl adipate, and petroleum solvents can be blended.

  The resin composition of the present invention is not particularly limited in its preparation method, and is prepared by measuring a predetermined amount of each of the aforementioned components and stirring and mixing them. For example, it can be prepared by mixing or melt-kneading using a roll kneader, a kneader, an extruder or the like after preliminary mixing.

  The resin composition of the present invention is not particularly limited in its curing method, and a conventionally known curing device such as a closed curing furnace or a tunnel furnace capable of continuous curing can be employed. The heating source is not particularly limited, and conventionally known methods such as hot air circulation, infrared heating, and high frequency heating can be employed. The curing temperature and the curing time may be set as appropriate.

  The use of the resin composition of the present invention is not particularly limited, and can be applied to various fields and products in which resin materials are used. Electrical / electronic materials use, building use, civil engineering use, automotive use Can be widely used for medical material applications.

  For example, examples of applications in electrical / electronic materials include adhesives, sealants, semiconductor sealants, insulating materials, heat conductive materials, hot melt materials, paints, potting agents, etc. For printed circuit boards, copper foil, copper-clad laminates, interlayer insulation materials, wiring coating films, resin-coated copper foil (RCC), prepreg and other electronic component sealing materials and layer forming materials, color filters, and flexible displays Films, resist materials, solder resist ink, display device forming materials such as alignment films, resist materials, semiconductor device forming materials such as buffer coat films, holograms, optical waveguides, optical circuits, optical circuit components, antireflection films, etc. Examples of the material for forming the optical component include.

  Examples of materials used in building applications include seals used for joints between exterior materials such as various metal panels and exterior materials such as siding boards, coating materials and primers, and exterior materials, base materials, ceiling materials, and interior materials. Materials, adhesives, injection materials, damping materials, soundproofing materials, conductive materials for shielding electromagnetic waves, putty materials, etc., adhesives for tiles and stone materials to outer wall materials and base materials, wood flooring materials for various floors Polymer material floor sheets, adhesives for floor tile adhesion, adhesives, cracking injection materials for various exterior materials and interior materials, etc. Examples of materials in civil engineering applications include roads, bridges, tunnels -Seals for breakwaters and various concrete products, coating materials, primers, paints, injection materials, putty materials, molding materials, spray materials, etc. Examples of materials in automotive applications include automobile bodies Sealing materials, coating materials, cushioning materials, damping materials, soundproofing materials, spraying materials, etc., automotive interior adhesives, adhesive materials, coating materials, foamed materials, etc., automotive parts sealing materials, adhesives, etc. Examples include sealing materials for various steel plate joints such as baths, adhesives, and coating materials. Examples of medical materials include medical rubber materials, medical adhesives, and medical device sealing materials.

(About surface treatment agent)
The surface treatment agent of the present invention is used for metal surface treatment and contains a triazine compound represented by the above chemical formula (II) as an active ingredient.
The triazine compound is prepared by dissolving or dispersing one or two or more different types in water, an organic solvent, or a mixture of water and an organic solvent.

  Examples of the organic solvent used for preparing the surface treatment agent of the present invention include methanol, ethanol, propanol, 2-propanol, butanol, ethylene glycol, propylene glycol, glycerin, diethylene glycol, triethylene glycol, ethylene glycol monomethyl ether, and ethylene glycol. Monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, acetone, tetrahydrofuran, dioxane, acetonitrile, dimethylformamide , Jimechi Acetamide, it can be exemplified dimethyl sulfoxide, can be used alone or in combination selected from these.

The concentration of the triazine compound represented by the chemical formula (II) in the surface treatment agent of the present invention is preferably in the range of 0.001 to 20% by weight.
When the concentration of the triazine compound is less than 0.001% by weight, the effect of improving the heat resistance and moisture resistance of the metal and the adhesion between the metal and the resin may not be sufficiently obtained. However, the effect of improving the heat resistance and moisture resistance of the metal and the adhesion between the metal and the resin has almost reached its peak, and the amount of the triazine compound is increased, which is not economical.

  As long as the effect of the present invention is not impaired, a known rust preventive or coupling agent may be added to the surface treatment agent of the present invention as necessary.

There is no restriction | limiting in particular as a method of making the surface treating agent of this invention contact the surface of a metal, Means, such as immersion, application | coating, a spray, can be employ | adopted.
The time (treatment time) for bringing the surface treatment agent into contact with the metal is preferably 1 second to 10 minutes. When the treatment time is less than 1 second, the film thickness of the chemical conversion film formed on the surface of the metal becomes thin, and there is a possibility that the heat resistance and moisture resistance of the metal and the adhesive force between the metal and the resin cannot be obtained sufficiently. is there. On the other hand, when the treatment time exceeds 10 minutes, there is no great difference in the film thickness of the chemical conversion film formed on the surface of the metal, and the effect of improving the heat resistance, moisture resistance and adhesion between the metal and the resin is also achieved. Almost reaches the peak.
Moreover, about the temperature of the surface treating agent at the time of making a surface treating agent contact the metal surface, it is preferable to set it as 5-50 degreeC, However, What is necessary is just to set suitably in relation to the said processing time.

  There is no particular limitation on the metal to be treated by the surface treating agent of the present invention, and for example, copper, aluminum, titanium, nickel, tin, iron, zinc, silver, platinum, gold and their alloys can be surface-treated. The copper alloy can be preferably surface treated.

EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention concretely, this invention is not limited to these.
The main raw materials used in these are as follows.

[raw materials]
2-Chloro-4,6-bis [(2-hydroxyethyl) amino] -1,3,5-triazine: synthesized according to the method described in Japanese Patent Publication No. 40-23025.
2-Mercapto-4,6-bis [(2-hydroxyethyl) amino] -1,3,5-triazine: Reference Example 1 shows a synthesis example.
2-Chloro-4,6-bis [(3-triethoxysilylpropyl) amino] -1,3,5-triazine: Reference Example 2 shows a synthesis example.
・ Sodium hydrosulfide: Wako Pure Chemical Industries, Ltd. ・ Cyanuric chloride: Same as above ・ Tetrahydrofuran: Same as above ・ Triethylamine: Same as above ・ 3-Aminopropyltriethoxysilane: Momentive Performance Materials ・ Bisphenol A type epoxy resin: Mitsubishi Chemical Product name "jER828"
-Silica: Product name "Aerosil 300" manufactured by Evonik
2-ethyl-4-methylimidazole: manufactured by Shikoku Kasei Kogyo Co., Ltd., trade name “2E4MZ”, hereinafter referred to as “2E4MZ”.
2,4-dimercapto-6-dipropylamino-1,3,5-triazine: synthesized according to the method described in “Japanese Patent Application Laid-Open No. 2014-237797”. Hereinafter, it is referred to as “DMDPAT”.

[Reference Example 1]
<Synthesis of 2-mercapto-4,6-bis [(2-hydroxyethyl) amino] -1,3,5-triazine>
In a 1 L flask equipped with a thermometer, 58.42 g (0.25 mol) of 2-chloro-4,6-bis [(2-hydroxyethyl) amino] -1,3,5-triazine, 250.0 g of water and water 20.0 g (0.25 mol) of sodium sulfide was added. The resulting solution was stirred at 100 ° C. for 3 hours. Next, the reaction solution is cooled to 10 ° C. or lower under ice-cooling, and the produced crystals are filtered off and dried, and the title triazine compound (hereinafter referred to as “triazine compound A”, see chemical formula (VI)). ) 36.7 g (yield 64%) was obtained.

[Reference Example 2]
<Synthesis of 2-chloro-4,6-bis [(3-triethoxysilylpropyl) amino] -1,3,5-triazine>
A 500 mL flask equipped with a thermometer was charged with 18.4 g (0.1 mol) of cyanuric chloride and 200.0 g of tetrahydrofuran, and cooled to 10 ° C. or lower under ice cooling with stirring. 44.3 g (0.2 mol) of triethoxysilane and 22.3 g (0.22 mol) of triethylamine were added dropwise in this order.
The resulting solution was stirred at 40 ° C. for 3 hours. The reaction mixture was then cooled to 10 ° C. or lower under ice cooling, and the insoluble material was filtered off and concentrated to obtain 111.0 g of the title triazine compound.

[Example 1]
<Synthesis of 2-mercapto-4,6-bis [(3-triethoxysilylpropyl) amino] -1,3,5-triazine>
In a 200 mL flask equipped with a thermometer, 11.1 g (0.02 mol) of 2-chloro-4,6-bis [(3-triethoxysilylpropyl) amino] -1,3,5-triazine, 20.0 g of tetrahydrofuran And 20.0 g (0.02 mol) of sodium hydrosulfide were added. The resulting solution was stirred at 70 ° C. for 6 hours. The insoluble material was then filtered off and concentrated to obtain 6.6 g of light yellow crystals (yield 60%).

The ¹ H-NMR spectrum data of the obtained crystal was as follows.
・¹ H-NMR (d ₆ -DMSO) δ: 7.75 (br, 2H), 4.32 (br, 1H), 3.73 (q, 12H), 3.18 (t, 4H), 1.38 (dt, 4H), 1.10 ( t, 18H), 0.57 (t, 4H).
The IR spectrum data of this crystal was as shown in the chart shown in FIG.
From these spectral data, the obtained crystal was identified as the title triazine compound represented by the chemical formula (VII) (hereinafter referred to as “triazine compound B”).

[ Reference Example 3 ]
A bisphenol A type epoxy resin, a triazine compound A, silica, and 2E4MZ were blended so as to have the composition shown in Table 1, and stirred and mixed for 5 minutes with a rotating and rotating mixer (Sinky Co., Ltd., trade name: Awatori Rentaro) An epoxy resin composition was prepared by defoaming for 1 minute.
The epoxy resin composition was uniformly applied to a steel plate, heated at 60 ° C. for 4 hours, and then heated and cured at 150 ° C. for 4 hours to prepare a test piece on which a cured film was formed.
About the obtained test piece, the tensile shear adhesive force was measured based on JISK6850, and the adhesiveness (adhesion) with respect to the steel plate of a hardened film was evaluated.
The test results obtained were as shown in Table 1.

[Example 2 ]
Except that triazine compound B was used instead of triazine compound A, an epoxy resin composition having the composition described in Table 1 was prepared in the same manner as in Reference Example 3, and then a test piece was prepared to obtain a cured film. The adhesion (adhesiveness) to the steel sheet was evaluated.
The test results obtained were as shown in Table 1.

[Comparative Example 1]
Except not using the triazine compound A, an epoxy resin composition having the composition shown in Table 1 was prepared in the same manner as in Reference Example 3, and then a test piece was prepared, and the adhesion of the cured film to the steel sheet ( Adhesion) was evaluated.
The test results obtained were as shown in Table 1.

[Comparative Example 2]
An epoxy resin composition having the composition shown in Table 1 was prepared in the same manner as in Reference Example 3 except that DMDPAT represented by the chemical formula (VIII) was used instead of the triazine compound A, and then a test piece was prepared. Then, the adhesiveness (adhesiveness) of the cured film to the steel plate was evaluated.
The test results obtained were as shown in Table 1.

  According to the test results shown in Table 1, the epoxy resin composition of the present invention can give a cured product having excellent adhesion performance.

Since the resin composition of the present invention can be suitably used as a raw material for adhesives, sealants, semiconductor encapsulants, copper-clad laminates, interlayer insulating materials, copper foils with resin (RCC), prepregs, etc. Industrial applicability is enormous.

Claims (13)

Triazine compound represented by Structural Formula (II).

(In the formula, Y may be the same or different and each represents a hydrogen atom or Si (OR ² ) _3. R ¹ and R ² may be the same or different from each other, and represent a hydrogen atom or a carbon atom. And represents an alkyl group having 1 to 6. q may be the same or different from each other, and represents an integer of 0 to 10. The method for synthesizing the triazine compound represented by the chemical formula (II) according to claim 1 , wherein the triazine compound represented by the chemical formula (IV) is reacted with sodium hydrosulfide.

(In the formula, Y, R ¹ and q are the same as described above.) A resin composition comprising a triazine compound represented by the chemical formula (II) according to claim 1 . A resin composition for an adhesive or a sealant comprising a triazine compound represented by the chemical formula (II) according to claim 1 . A resin composition for a semiconductor encapsulant comprising a triazine compound represented by the chemical formula (II) according to claim 1 . A surface treatment agent comprising a triazine compound represented by the chemical formula (II) according to claim 1 . A solder resist ink comprising a triazine compound represented by the chemical formula (II) according to claim 1 . A copper foil, wherein the surface treatment agent according to claim 6 is applied to the surface . Copper clad laminate is characterized in that using the claim 3, wherein the resin composition. An interlayer insulating material using the resin composition according to claim 3 . A resin-coated copper foil using the resin composition according to claim 3 . A prepreg characterized in that the resin composition according to claim 3 is applied to the surface of a sheet-like reinforcing base material or impregnated in the reinforcing base material . A printed wiring board, wherein the surface treatment agent according to claim 6 is applied to the surface .

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