JP6462539B2 - Triazine compound, method for synthesizing the compound and use thereof - Google Patents
Triazine compound, method for synthesizing the compound and use thereof Download PDFInfo
- Publication number
- JP6462539B2 JP6462539B2 JP2015174738A JP2015174738A JP6462539B2 JP 6462539 B2 JP6462539 B2 JP 6462539B2 JP 2015174738 A JP2015174738 A JP 2015174738A JP 2015174738 A JP2015174738 A JP 2015174738A JP 6462539 B2 JP6462539 B2 JP 6462539B2
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- Prior art keywords
- triazine compound
- triazine
- materials
- compound represented
- resin composition
- Prior art date
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- -1 Triazine compound Chemical class 0.000 title claims description 60
- 238000000034 method Methods 0.000 title claims description 8
- 230000002194 synthesizing effect Effects 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 title description 11
- 239000000463 material Substances 0.000 claims description 48
- 239000000126 substance Substances 0.000 claims description 37
- 229920005989 resin Polymers 0.000 claims description 33
- 239000011347 resin Substances 0.000 claims description 33
- 239000011342 resin composition Substances 0.000 claims description 24
- 239000000853 adhesive Substances 0.000 claims description 17
- 230000001070 adhesive effect Effects 0.000 claims description 17
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 14
- 239000012756 surface treatment agent Substances 0.000 claims description 13
- 239000011889 copper foil Substances 0.000 claims description 8
- 239000011810 insulating material Substances 0.000 claims description 7
- 239000004065 semiconductor Substances 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 239000000565 sealant Substances 0.000 claims description 6
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000011229 interlayer Substances 0.000 claims description 4
- 230000003014 reinforcing effect Effects 0.000 claims description 4
- 229910000679 solder Inorganic materials 0.000 claims description 4
- 239000008393 encapsulating agent Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003822 epoxy resin Substances 0.000 description 34
- 229920000647 polyepoxide Polymers 0.000 description 34
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- 239000002184 metal Substances 0.000 description 18
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 9
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- 230000000694 effects Effects 0.000 description 8
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 4
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
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- 239000005011 phenolic resin Substances 0.000 description 4
- 229920003192 poly(bis maleimide) Polymers 0.000 description 4
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- 229920001225 polyester resin Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NARDEJGFHDQCKP-UHFFFAOYSA-N 6-chloro-2-N,4-N-bis(3-triethoxysilylpropyl)-1,3,5-triazine-2,4-diamine Chemical compound CCO[Si](CCCNC1=NC(NCCC[Si](OCC)(OCC)OCC)=NC(Cl)=N1)(OCC)OCC NARDEJGFHDQCKP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
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- 238000013329 compounding Methods 0.000 description 3
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- XWGOYJWQFZCFNN-UHFFFAOYSA-N 2-[[4-chloro-6-(2-hydroxyethylamino)-1,3,5-triazin-2-yl]amino]ethanol Chemical compound OCCNC1=NC(Cl)=NC(NCCO)=N1 XWGOYJWQFZCFNN-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
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Images
Description
本発明は、新規なトリアジン化合物、該化合物の合成方法および該化合物を使用する用途に関する。 The present invention relates to a novel triazine compound, a method for synthesizing the compound, and an application using the compound.
エポキシ樹脂、フェノール樹脂、ポリエステル樹脂等のポリマーは、熱硬化性であって且つ耐腐食性、電気絶縁性に優れているため、電子部品やプリント基板関連の分野において、接着剤、導電性ペースト、レジストインクや、封止材、絶縁材、基板用マトリックス材等の原料として、広く使用されている。
しかしながら、このようなポリマーは、マイグレーションを抑制する機能、即ち絶縁材上の配線（回路）や電極を構成する金属が、高湿度の環境下において、電位差により絶縁材上を移行する現象を抑える機能に乏しいため、電子部品やプリント基板の絶縁不良を招来すると云う難点があった。
また、それらのポリマーと、銅等の金属材料やガラス基板等の無機材料との、更なる密着性の改善も求められていた。
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.
このような課題を解決するための添加剤として、種々の物質が使用されている。中でもトリアジン骨格を有する物質が、前記のマイグレーションの抑制や、種々の金属との密着性の改善に有効であるとされている。
例えば、特許文献１には１分子中に２個のメルカプト基を有するトリアジン化合物を含む半導体封止用エポキシ樹脂組成物が提案されている。また、特許文献２には２−メルカプト−Ｓ−トリアジン誘導体の製造法が提案されている。
しかしながら、これらのトリアジン化合物に由来する密着性改善効果は未だ十分とは言えなかった。
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,
However, the adhesion improving effect derived from these triazine compounds has not been sufficient yet.
本発明は、優れた密着性向上効果を発揮するトリアジン化合物、該化合物の合成方法、そして、種々の用途が期待される該化合物を含有する樹脂組成物ならびに表面処理剤を提供することを目的とする。 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.
本発明者らは、前記の課題を解決するために鋭意研究を重ねた結果、メルカプト基と特定の基により置換されたアミノ基を有するトリアジン化合物とすることにより、所期の目的を達成し得ることを見出し、本発明を完成するに至ったものである。
即ち、第１の発明は、化学式（II）で示されるトリアジン化合物である。
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).
第２の発明は、化学式（IV）で示されるトリアジン化合物と、水硫化ナトリウムを反応させることを特徴とする第１の発明の化学式（II）で示されるトリアジン化合物の合成方法である。 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.
第３の発明は、第１の発明の化学式（II）で示されるトリアジン化合物を含有することを特徴とする樹脂組成物である。 A third invention is a resin composition comprising a triazine compound represented by the chemical formula (II) of the first invention .
第４の発明は、第１の発明の化学式（II）で示されるトリアジン化合物を含有することを特徴とする接着剤用またはシール剤用樹脂組成物である。 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 .
第５の発明は、第１の発明の化学式（II）で示されるトリアジン化合物を含有することを特徴とする半導体封止剤用樹脂組成物である。 5th invention is a resin composition for semiconductor sealing agents characterized by containing the triazine compound shown by Chemical formula (II) of 1st invention .
第６の発明は、第１の発明の化学式（II）で示されるトリアジン化合物を含有することを特徴とする表面処理剤である。 6th invention is a surface treating agent characterized by containing the triazine compound shown by chemical formula (II) of 1st invention .
第７の発明は、第１の発明の化学式（II）で示されるトリアジン化合物を含有することを特徴とするソルダーレジストインクである。 A seventh invention is a solder resist ink characterized by containing a triazine compound represented by the chemical formula (II) of the first invention .
第８の発明は、第６の発明の表面処理剤を表面に塗布したことを特徴とする銅箔である。 An eighth invention is a copper foil characterized in that the surface treatment agent of the sixth invention is applied to the surface.
第９の発明は、第３の発明の樹脂組成物を使用したことを特徴とする銅張積層板である。 The ninth invention is a copper-clad laminate characterized by using the resin composition of the third invention.
第１０の発明は、第３の発明の樹脂組成物を使用したことを特徴とする層間絶縁材料である。 The tenth invention is an interlayer insulating material characterized by using the resin composition of the third invention.
第１１の発明は、第３の発明の樹脂組成物を使用したことを特徴とする樹脂付銅箔である。 An eleventh invention is a copper foil with a resin characterized by using the resin composition of the third invention.
第１２の発明は、第３の発明の樹脂組成物をシート状補強基材の表面に塗布または該補強基材中に含浸したことを特徴とするプリプレグである。 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.
第１３の発明は、第６の発明の表面処理剤を表面に塗布したことを特徴とするプリント配線板である。 A thirteenth invention is a printed wiring board characterized in that the surface treating agent of the sixth invention is applied to the surface.
本発明のトリアジン化合物を、エポキシ樹脂、フェノール樹脂、ポリエステル樹脂、アクリル樹脂、ポリスチレン樹脂、エポキシ(メタ)アクリレート樹脂、ポリイミド樹脂、ビスマレイミド樹脂、ビスマレイミドトリアジン樹脂、シアネートエステル樹脂、シクロオレフィン樹脂、ポリフェニレンエーテル樹脂、ベンゾオキサジン樹脂、フッ素樹脂等のポリマーの添加剤として使用した場合には、当該トリアジン化合物がポリマー中に溶解または均一に分散して、電子部品やプリント配線板等のマイグレーションを抑制する効果や、電子部品あるいはプリント配線板を構成する銅、アルミニウム、チタン、ニッケル、スズ、鉄、亜鉛、銀、白金、金等の金属材料および無機材料と、ポリマーとの密着性を高める効果を発揮することが期待される。
また、本発明のトリアジン化合物を含有する表面処理剤を、銅箔およびプリント配線板に塗布した場合には、電子部品あるいはプリント配線板を構成する銅、アルミニウム、チタン、ニッケル、スズ、鉄、亜鉛、銀、白金、金等の金属材料および無機材料と、ポリマーとの密着性を高める効果を発揮することが期待される。
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.
以下、本発明を詳細に説明する。
本発明のトリアジン化合物は、前記の化学式（II）で示される。
Hereinafter, the present invention will be described in detail.
Triazine compounds of the present invention is represented by the above-mentioned chemical formula (II).
化学式（II）で示されるトリアジン化合物の例としては、
２−メルカプト−４，６−ビス（アルコキシシリルメチルアミノ）−１，３，５−トリアジン、
２−メルカプト−４，６−ビス［（２−アルコキシシリルエチル）アミノ］−１，３，５−トリアジン、
２−メルカプト−４，６−ビス［（３−アルコキシシリルプロピル）アミノ］−１，３，５−トリアジン、
２−メルカプト−４，６−ビス［（４−アルコキシシリルブチル）アミノ］−１，３，５−トリアジン、
２−メルカプト−４，６−ビス［（５−アルコキシシリルペンチル）アミノ］−１，３，５−トリアジン、
２−メルカプト−４，６−ビス［（６−アルコキシシリルヘキシル）アミノ］−１，３，５−トリアジン、
２−メルカプト−４，６−ビス［（８−アルコキシシリルオクチル）アミノ］−１，３，５−トリアジン、
２−メルカプト−４，６−ビス［（１０−アルコキシシリルデシル）アミノ］−１，３，５−トリアジン、
２−メルカプト−４，６−ビス［（３−ヒドロキシシリルプロピル）アミノ］−１，３，５−トリアジン等が挙げられる。
なお、ここで云うアルコキシは、メトキシ、エトキシ、プロポキシ、ブトキシ等を指す。
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.
化学式（II）で示されるトリアジン化合物は、前記の化学式（IV）で示されるトリアジン化合物と、水硫化ナトリウムを、適量の反応溶媒中において、適宜の反応温度および反応時間にて反応させることにより合成することができる。 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.
化学式（IV）で示されるトリアジン化合物の例としては、
２−クロロ−４，６−ビス（アルコキシシリルメチルアミノ）−１，３，５−トリアジン、
２−クロロ−４，６−ビス［（２−アルコキシシリルエチル）アミノ］−１，３，５−トリアジン、
２−クロロ−４，６−ビス［（３−アルコキシシリルプロピル）アミノ］−１，３，５−トリアジン、
２−クロロ−４，６−ビス［（４−アルコキシシリルブチル）アミノ］−１，３，５−トリアジン、
２−クロロ−４，６−ビス［（５−アルコキシシリルペンチル）アミノ］−１，３，５−トリアジン、
２−クロロ−４，６−ビス［（６−アルコキシシリルヘキシル）アミノ］−１，３，５−トリアジン、
２−クロロ−４，６−ビス［（８−アルコキシシリルオクチル）アミノ］−１，３，５−トリアジン、
２−クロロ−４，６−ビス［（１０−アルコキシシリルデシル）アミノ］−１，３，５−トリアジン等が挙げられる。
なお、ここで云うアルコキシは、メトキシ、エトキシ、プロポキシ、ブトキシ等を指す。
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.
前記の水硫化ナトリウムは、化学式（IV）で示されるトリアジン化合物１モルに対して、通常、１．０〜２．０モルの範囲で用いられる。
Sodium water sulfate of said
前記の反応溶媒の例としては、メタノール、エタノール等のアルコール系溶剤、クロロホルム、ジクロロメタン等のハロゲン系溶剤、トルエン、ヘキサン等の炭化水素系溶剤、テトラヒドロフラン、１，４−ジオキサン等のエーテル系溶剤およびジメチルスルホキシド（ＤＭＳＯ）等が挙げられる。 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).
前記の反応温度については、１０〜１２０℃の範囲内で適宜設定することができる。また、前記の反応時間については、設定した反応温度に応じて適宜決定されるが、０．５〜２４時間とすることが好ましく、１〜６時間とすることがより好ましい。 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.
化学式（IV）で示されるトリアジン化合物と、水硫化ナトリウムによる反応の後、得られた反応混合物から、例えば、晶析操作または抽出操作によって、目的とするトリアジン化合物を得ることができる。必要に応じて、更に、水等の溶媒による洗浄や活性炭処理等によって、目的とするトリアジン化合物を精製することができる。 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.
（樹脂組成物について）
前記の化学式（II）で示されるトリアジン化合物は、硬化剤と共に、更に必要に応じて硬化剤および硬化促進剤（硬化触媒）と共に、樹脂に１種または種類の異なる２種以上配合して、樹脂組成物とすることができる。
(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.
化学式（II）で示されるトリアジン化合物を含有する本発明の樹脂組成物（接着剤用、シール剤用および半導体封止剤用）における該トリアジン化合物の配合量は、樹脂１００重量部に対して、０．０１〜１５０重量部の割合とすることが好ましく、０．１〜５０重量部の割合とすることがより好ましい。
そして、硬化剤の配合量は、樹脂１００重量部に対して、０．０１〜３００重量部の割合とすることが好ましく、０．１〜２００重量部の割合とすることがより好ましい。
また、硬化促進剤の配合量は、樹脂１００重量部に対して０．０１〜２重量部の割合とすることが好ましく、０．１〜０．５重量部の割合とすることがより好ましい。
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.
前記の樹脂の例としては、エポキシ樹脂、フェノール樹脂、ポリエステル樹脂、アクリル樹脂、ポリスチレン樹脂、エポキシ(メタ)アクリレート樹脂、ポリイミド樹脂、ビスマレイミド樹脂、ビスマレイミドトリアジン樹脂、シアネートエステル樹脂、シクロオレフィン樹脂、ポリフェニレンエーテル樹脂、ベンゾオキサジン樹脂、フッ素樹脂等が挙げられる。
これらの樹脂の中でも特に、エポキシ樹脂が好ましい。
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.
前記のエポキシ樹脂としては、分子内に少なくとも２つのエポキシ基を有する物質であればよいが、分子内に少なくとも２つのエポキシ基を有する物質と、分子内に１つのエポキシ基を有する物質の混合物であってもよい。
このようなエポキシ樹脂の例としては、
ビスフェノールＡ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂、フェノールノボラック型エポキシ樹脂やクレゾールノボラック型エポキシ樹脂等のノボラック型エポキシ樹脂、脂環式エポキシ樹脂、３′，４′−エポキシシクロヘキシルメチル−３，４−エポキシシクロヘキサンカルボキシレートのような環状脂環式エポキシ樹脂、１，３，４，６−テトラグリシジルグリコールウリル、１，３，４，６−テトラグリシジル−３ａ，６ａ−ジメチルグリコールウリル、１，３，４，６−テトラグリシジル−３ａ，６ａ−ジフェニルグリコールウリル、トリグリシジルイソシアヌレート、モノアリルジグリシジルイソシアヌレート、ジアリルモノグリシジルイソシアヌレートやヒダントイン型エポキシ樹脂等の含窒素環状エポキシ樹脂、水添ビスフェノールＡ型エポキシ樹脂、脂肪族系エポキシ樹脂、グリシジルエーテル型エポキシ樹脂、ビスフェノールＳ型エポキシ樹脂、ビフェニル型エポキシ樹脂、ジシクロ環型エポキシ樹脂、ナフタレン型エポキシ樹脂やハロゲン化エポキシ樹脂等の他、炭素−炭素二重結合およびグリシジル基を有する有機化合物と、ＳｉＨ基を有するケイ素化合物とのヒドロシリル化付加反応によるエポキシ変性オルガノポリシロキサン化合物（例えば、特開２００４−９９７５１号公報や特開２００６−２８２９８８号公報に開示されたエポキシ変性オルガノポリシロキサン化合物）が挙げられる。
なお、ここで云うエポキシ樹脂とは、硬化前のエポキシ化合物を指す。
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.
前記の硬化剤の例としては、
フェノール性水酸基を有する化合物、酸無水物やアミン類の他、メルカプトプロピオン酸エステル、エポキシ樹脂末端メルカプト化合物等のメルカプタン化合物、トリフェニルホスフィン、ジフェニルナフチルホスフィン、ジフェニルエチルホスフィン等の有機ホスフィン化合物、芳香族ホスホニウム塩、芳香族ジアゾニウム塩、芳香族ヨードニウム塩、芳香族セレニウム塩等が挙げられる。
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.
前記のフェノール性水酸基を有する化合物の例としては、
ビスフェノールＡ、ビスフェノールＦ、ビスフェノールＳ、テトラメチルビスフェノールＡ、テトラメチルビスフェノールＦ、テトラメチルビスフェノールＳ、テトラクロロビスフェノールＡ、テトラブロモビスフェノールＡ、ジヒドロキシナフタレン、フェノールノボラック、クレゾールノボラック、ビスフェノールＡノボラック、臭素化フェノールノボラック、レゾルシノール等が挙げられる。
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.
前記の酸無水物の例としては、
メチルテトラヒドロ無水フタル酸、メチルヘキサヒドロ無水フタル酸、ヘキサヒドロ無水フタル酸、５−ノルボルネン−２，３−ジカルボン酸無水物、無水トリメリット酸、ナジック酸無水物、ハイミック酸無水物、メチルナジック酸無水物、メチルビシクロ［２．２．１］ヘプタン−２，３−ジカルボン酸無水物、ビシクロ［２．２．１］ヘプタン−２，３−ジカルボン酸無水物、メチルノルボルナン−２，３−ジカルボン酸無水物等が挙げられる。
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.
前記のアミン類の例としては、
ジエチレンジアミン、トリエチレンテトラミン、ヘキサメチレンジアミン、ダイマー酸変性エチレンジアミン、４，４′−ジアミノジフェニルスルホン、４，４′−ジアミノジフェノールエーテル、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等や、２−メチルイミダゾール、２−エチル−４−メチルイミダゾール、２−フェニルイミダゾール等のイミダゾール化合物が挙げられる。
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.
前記の硬化促進剤の例としては、
１，８−ジアザビシクロ［５．４．０］−７−ウンデセン、ジエチレントリアミン、トリエチレンテトラミン、ベンジルジメチルアミン、トリエタノールアミン、ジメチルアミノエタノール、トリス(ジメチルアミノメチル)フェノール等のアミン化合物、２−メチルイミダゾール、２−フェニルイミダゾール、２−フェニル−４−メチルイミダゾール、２−ヘプタデシルイミダゾール等のイミダゾール化合物、トリブチルホスフィン、メチルジフェニルホスフィン、トリフェニルホスフィン、ジフェニルホスフィン、フェニルホスフィン等の有機ホスフィン化合物、テトラブチルホスフォニウムブロマイド、テトラブチルホスホニウムジエチルホスホロジチオネート等のホスホニウム化合物、テトラフェニルホスホニウム・テトラフェニルボレート、２−メチル−４−メチルイミダゾール・テトラフェニルボレート、Ｎ−メチルモルホリン・テトラフェニルボレート等のテトラフェニルボロン塩、酢酸鉛、オクチル酸錫、ヘキサン酸コバルト等の脂肪族酸金属塩等が挙げられる。
なお、これらの物質のうちの一部は、前述の硬化剤としても使用される。
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.
本発明の樹脂組成物には、必要に応じて非晶性シリカ、結晶性シリカ、炭酸カルシウム、炭酸マグネシウム、アルミナ、マグネシア、クレー、タルク、ケイ酸カルシウム、酸化チタン等の無機充填材、セルロース、ガラス繊維、ボロン繊維、炭素繊維等の繊維状充填材、カーボンブラック、グラファイト、カーボンナノチューブ、フラーレン、酸化鉄、金、銀、アルミニウム粉、鉄粉、ニッケル、銅、亜鉛、クロム、半田、ナノサイズの金属結晶、金属間化合物等の導電性充填材、エチレングリコール、プロピレングリコール等の脂肪族ポリオール、脂肪族または芳香族カルボン酸化合物、フェノール化合物等の炭酸ガス発生防止剤、ポリアルキレングリコール等の可撓性付与剤、酸化防止剤、可塑剤、滑剤、シラン系等のカップリング剤、無機充填材の表面処理剤、難燃剤、帯電防止剤、着色剤、レベリング剤、イオントラップ剤、摺動性改良剤、各種ゴム、耐衝撃性改良剤、揺変性付与剤、界面活性剤、表面張力低下剤、消泡剤、沈降防止剤、光拡散剤、紫外線吸収剤、抗酸化剤、離型剤、蛍光剤等の添加剤を配合することができる。
また、主成分の樹脂を改質して、その特性を改良するために、フェノール樹脂、ポリエステル樹脂、アクリル樹脂、ポリスチレン樹脂、ポリウレタン樹脂、ポリエーテル樹脂、メラミン樹脂、アクリル変性エポキシ樹脂、ウレタン変性エポキシ樹脂、ゴム変性エポキシ樹脂、アルキッド変性エポキシ樹脂等から選択される主成分の樹脂とは異なる樹脂を、配合することができる。
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.
また、本発明の樹脂組成物には、該樹脂組成物の溶剤（溶液）化や粘度調整の為に、トルエン、キシレン、メチルエチルケトン、メチルイソブチルケトン、酢酸エチル、酢酸ブチル等の有機溶剤、ブチルグリシジルエーテル、Ｎ，Ｎ′−ジグリシジル−ｏ−トルイジン、フェニルグリシジルエーテル、スチレンオキサイド、エチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、１，６−ヘキサンジオールジグリシジルエーテル等の反応性希釈剤、ジオクチルフタレート、ジブチルフタレート、ジオクチルアジベート、石油系溶剤等の非反応性の希釈剤を配合することができる。 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.
本発明の樹脂組成物は、その調製方法に特に制限はなく、前述の各成分を所定量計り取って撹拌混合することにより調製される。例えば、予備混合の後、ロール混練機、ニーダーや押出機等を用いて、混合あるいは溶融混練することにより調製することもできる。 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.
本発明の樹脂組成物は、その硬化方法に特に制限はなく、密閉式硬化炉や連続硬化が可能なトンネル炉等の従来公知の硬化装置を採用することができる。加熱源についても特に制約されることなく、熱風循環、赤外線加熱、高周波加熱等、従来公知の方法を採用することができる。硬化温度および硬化時間は、適宜設定すればよい。 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.
本発明の樹脂組成物の使用用途に特に制限はなく、樹脂製材料が使用される様々な分野、製品に適用することが可能であり、電気・電子材料用途、建築用途、土木用途、自動車用途、医療材料用途等に広く使用できる。 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.
例えば、電気・電子材料用途における例としては、接着剤、シール剤、半導体封止剤、絶縁材料、熱伝導性材料、ホットメルト材料、塗料、ポッティング剤等が挙げられるが、より具体的には、プリント配線板、銅箔、銅張積層板、層間絶縁材料、配線被覆膜、樹脂付銅箔（ＲＣＣ）、プリプレグ等の電子部品の封止材料や層形成材料、カラーフィルター、フレキシブルディスプレイ用フィルム、レジスト材料、ソルダーレジストインク、配向膜等の表示装置の形成材料、レジスト材料、バッファーコート膜等の半導体装置の形成材料、ホログラム、光導波路、光回路、光回路部品、反射防止膜等の光学部品の形成材料が挙げられる。 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.
また、建築用途における材料の例としては、各種金属パネル・サイディングボード等の外装材の目地用シール材、コーティング材、プライマー等、外装材・下地材・天井材と内装材の間に使用するシール材、接着剤、注入材、制振材、防音材、電磁波遮蔽用導電性材料、パテ材等、外壁材・下地材へのタイル・石材接着用の接着剤、各種床への木質フローリング材・高分子材料系床シート・床タイル接着用の接着剤、粘着剤等、各種外装材・内装材のクラック補修用注入材等が挙げられ、土木用途における材料の例としては、道路・橋梁・トンネル・防波堤・各種コンクリート製品の目地用シール材、コーティング材、プライマー、塗料、注入材、パテ材、型取材、吹付材等が挙げられ、自動車用途における材料の例としては、自動車ボディーのシール材、コーティング材、緩衝材、制振材、防音材、吹付材等、自動車内装用の接着剤、粘着材、コーティング材、発泡材料等、自動車部品のシール材、接着剤等、トラック・バス等の各種鋼板継ぎ目用のシール材、接着剤、コーティング材等が挙げられ、医療材料用途における例としては、医療用ゴム材料、医療用粘着剤、医療機器シール材等が挙げられる。 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.
（表面処理剤について）
本発明の表面処理剤は、金属の表面処理に使用され、前記の化学式（II）で示されるトリアジン化合物を有効成分として含有する。
該トリアジン化合物は、１種もしくは種類の異なる２種以上を水、有機溶剤もしくは水と有機溶剤の混合液に溶解または分散することにより調製される。
(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.
本発明の表面処理剤の調製に使用される有機溶剤としては、メタノール、エタノール、プロパノール、２−プロパノール、ブタノール、エチレングリコール、プロピレングリコール、グリセリン、ジエチレングリコール、トリエチレングリコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、アセトン、テトラヒドロフラン、ジオキサンの他、アセトニトリル、ジメチルホルムアミド、ジメチルアセトアミド、ジメチルスルホキシド等を例示することができ、これらから選択される１種または２種以上を使用することができる。 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.
本発明の表面処理剤中における化学式（II）で示されるトリアジン化合物の濃度は、０．００１〜２０重量％の範囲であることが好ましい。
該トリアジン化合物の濃度が０．００１重量％未満の場合、金属の耐熱性、耐湿性および金属と樹脂との接着性の向上効果が十分に得られない虞があり、２０重量％を超える場合には、金属の耐熱性、耐湿性および金属と樹脂との接着性の向上効果がほぼ頭打ちとなり、トリアジン化合物の使用量が増えるばかりで経済的ではない。
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.
本発明の表面処理剤には、本発明の効果を損なわない限りにおいて、必要により公知の防錆剤やカップリング剤等を加えてもよい。 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.
本発明の表面処理剤を金属の表面に接触させる方法としては、特に制限はなく、浸漬、塗布、スプレー等の手段を採用することができる。
表面処理剤と金属を接触させる時間（処理時間）については、１秒〜１０分とすることが好ましい。処理時間が１秒未満の場合には、金属の表面に形成される化成皮膜の膜厚が薄くなり、金属の耐熱性、耐湿性および金属と樹脂との接着力が十分に得られない虞がある。一方、処理時間が１０分を超えた場合には、金属の表面に形成される化成皮膜の膜厚に大差はなく、金属の耐熱性、耐湿性および金属と樹脂との接着性の向上効果もほぼ頭打ちとなる。
また、表面処理剤を金属の表面に接触させる際の表面処理剤の温度については、５〜５０℃とすることが好ましいが、前記の処理時間との関係において、適宜設定すればよい。
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.
本発明の表面処理剤により処理される金属に特に制限はなく、例えば、銅、アルミニウム、チタン、ニッケル、スズ、鉄、亜鉛、銀、白金、金やそれらの合金を表面処理できるが、銅または銅合金を好ましく表面処理することができる。 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.
以下、本発明を実施例および比較例によって具体的に説明するが、本発明はこれらに限定されるものではない。
また、これらにおいて使用した主な原材料は以下のとおりである。
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.
［原材料］
・２−クロロ−４，６−ビス［（２−ヒドロキシエチル）アミノ］−１，３，５−トリアジン：「特公昭４０−２３０２５号公報」に記載の方法に準拠して合成した。
・２−メルカプト−４，６−ビス［（２−ヒドロキシエチル）アミノ］−１，３，５−トリアジン：参考例１に合成例を示した。
・２−クロロ−４，６−ビス［（３−トリエトキシシリルプロピル）アミノ］−１，３，５−トリアジン：参考例２に合成例を示した。
・水硫化ナトリウム：和光純薬工業社製
・塩化シアヌル：同上
・テトラヒドロフラン：同上
・トリエチルアミン：同上
・３−アミノプロピルトリエトキシシラン：モメンティブ・パフォーマンス・マテリアルズ社製
・ビスフェノールＡ型エポキシ樹脂：三菱化学社製、商品名「ｊＥＲ８２８」
・シリカ：エボニック社製、商品名「アエロジル３００」
・２−エチル−４−メチルイミダゾール：四国化成工業社製、商品名「２Ｅ４ＭＺ」、以下「２Ｅ４ＭＺ」と云う。
・２，４−ジメルカプト−６−ジプロピルアミノ−１，３，５−トリアジン：「特開２０１４−２３７７９７号公報」に記載の方法に準拠して合成した。以下「ＤＭＤＰＡＴ」と云う。
[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”.
〔参考例１〕
＜２−メルカプト−４，６−ビス［（２−ヒドロキシエチル）アミノ］−１，３，５−トリアジンの合成＞
温度計を備えた１Ｌフラスコに、２−クロロ−４，６−ビス［（２−ヒドロキシエチル）アミノ］−１，３，５−トリアジン５８．４２ｇ（０．２５ｍｏｌ）、水２５０．０ｇおよび水硫化ナトリウム２０．０ｇ（０．２５ｍｏｌ）を投入した。得られた溶液を１００℃にて３時間撹拌した。次いで、反応液を氷冷下で１０℃以下になるまで冷却して、生成した結晶をろ別し、乾燥して、表題のトリアジン化合物（以下「トリアジン化合物Ａ」と云う、化学式（VI）参照）３６．７ｇ（収率６４％）を得た。
[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.
〔参考例２〕
＜２−クロロ−４，６−ビス［（３−トリエトキシシリルプロピル）アミノ］−１，３，５−トリアジンの合成＞
温度計を備えた５００ｍＬフラスコに、塩化シアヌル１８．４ｇ（０．１ｍｏｌ）とテトラヒドロフラン２００．０ｇを投入して、撹拌しながら氷冷下で１０℃以下になるまで冷却した後、３−アミノプロピルトリエトキシシラン４４．３ｇ（０．２ｍｏｌ）、トリエチルアミン２２．３ｇ（０．２２ｍｏｌ）の順に滴下した。
得られた溶液を４０℃にて３時間撹拌した。次いで、反応液を氷冷下で１０℃以下になるまで冷却した後、不溶物をろ別し、濃縮して表題のトリアジン化合物１１１．０ｇを得た。
[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.
〔実施例１〕
＜２−メルカプト−４，６−ビス［（３−トリエトキシシリルプロピル）アミノ］−１，３，５−トリアジンの合成＞
温度計を備えた２００ｍＬフラスコに、２−クロロ−４，６−ビス［（３−トリエトキシシリルプロピル）アミノ］−１，３，５−トリアジン１１．１ｇ（０．０２ｍｏｌ）、テトラヒドロフラン２０．０ｇおよび水硫化ナトリウム２０．０ｇ（０．０２ｍｏｌ）を投入した。得られた溶液を７０℃にて６時間撹拌した。次いで不溶物をろ別し、濃縮して、淡黄色結晶６．６ｇ（収率６０％）を得た。
[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%).
得られた結晶の１Ｈ−ＮＭＲスペクトルデータは、以下のとおりであった。
・1H-NMR(d6-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).
また、この結晶のＩＲスペクトルデータは、図１に示したチャートのとおりであった。
これらのスペクトルデータより、得られた結晶は、化学式（VII）で示される表題のトリアジン化合物（以下「トリアジン化合物Ｂ」と云う。）であるものと同定した。
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”).
〔参考例３〕
ビスフェノールＡ型エポキシ樹脂、トリアジン化合物Ａ、シリカ、２Ｅ４ＭＺを表１記載の組成となるように配合し、自転公転ミキサー（シンキー社製、商品名：あわとり錬太郎）にて５分間撹拌混合し、１分間脱泡してエポキシ樹脂組成物を調製した。
エポキシ樹脂組成物を、鋼板に均一に塗布し、６０℃／４時間加熱した後、１５０℃／４時間加熱硬化させて、硬化皮膜が形成した試験片を作製した。
得られた試験片について、引張せん断接着力をＪＩＳＫ６８５０に準拠して測定し、硬化皮膜の鋼板に対する接着性（密着性）を評価した。
得られた試験結果は、表１に示したとおりであった。
[ 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.
〔実施例２〕
トリアジン化合物Ａの代わりにトリアジン化合物Ｂを使用した以外は、参考例３と同様にして、表１記載の組成を有するエポキシ樹脂組成物を調製し、続いて、試験片を調製して、硬化皮膜の鋼板に対する接着性（密着性）を評価した。
得られた試験結果は、表１に示したとおりであった。
[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.
〔比較例１〕
トリアジン化合物Ａを使用しない以外は、参考例３と同様にして、表１記載の組成を有するエポキシ樹脂組成物を調製し、続いて、試験片を調製して、硬化皮膜の鋼板に対する接着性（密着性）を評価した。
得られた試験結果は、表１に示したとおりであった。
[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.
〔比較例２〕
トリアジン化合物Ａの代わりに化学式（VIII）で示されるＤＭＤＰＡＴを使用した以外は、参考例３と同様にして、表１記載の組成を有するエポキシ樹脂組成物を調製し、続いて、試験片を調製して、硬化皮膜の鋼板に対する接着性（密着性）を評価した。
得られた試験結果は、表１に示したとおりであった。
[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.
表１に示した試験結果によれば、本発明のエポキシ樹脂組成物は、優れた接着性能を有する硬化物を与えることができる。 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.
本発明の樹脂組成物は、接着剤、シール剤、半導体封止材、銅張積層板、層間絶縁材料、樹脂付銅箔（ＲＣＣ）、プリプレグ等の原料として好適に利用することができるので、産業上の利用可能性は多大である。
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.
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