JPS63205313A - Curing agent for epoxy resin - Google Patents
Curing agent for epoxy resinInfo
- Publication number
- JPS63205313A JPS63205313A JP3790987A JP3790987A JPS63205313A JP S63205313 A JPS63205313 A JP S63205313A JP 3790987 A JP3790987 A JP 3790987A JP 3790987 A JP3790987 A JP 3790987A JP S63205313 A JPS63205313 A JP S63205313A
- Authority
- JP
- Japan
- Prior art keywords
- curing agent
- dicyandiamide
- epoxy resin
- diaminotriazine
- derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 31
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 16
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 16
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims abstract description 24
- WEWFIUPOLKEEJP-UHFFFAOYSA-N triazine-4,6-diamine Chemical class NC1=CC(N)=NN=N1 WEWFIUPOLKEEJP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 229910000679 solder Inorganic materials 0.000 abstract description 10
- 239000007788 liquid Substances 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 239000007795 chemical reaction product Substances 0.000 abstract description 4
- 239000000843 powder Substances 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 abstract description 3
- 238000007650 screen-printing Methods 0.000 abstract description 3
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 description 9
- 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 5
- 239000000976 ink Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000007747 plating Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- TZSXPFCNIIPDDY-UHFFFAOYSA-N 4-ethyltriazine Chemical compound CCC1=CC=NN=N1 TZSXPFCNIIPDDY-UHFFFAOYSA-N 0.000 description 1
- CPIVYSAVIPTCCX-UHFFFAOYSA-N 4-methylpentan-2-yl acetate Chemical compound CC(C)CC(C)OC(C)=O CPIVYSAVIPTCCX-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- -1 methyl ethyl Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RXTNIJMLAQNTEG-UHFFFAOYSA-N methylamyl acetate Natural products CCCCC(C)OC(C)=O RXTNIJMLAQNTEG-UHFFFAOYSA-N 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、エポキシ樹脂用硬化剤に関するもの１゜であ
る。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a curing agent for epoxy resins.
従来、電子部品用エポキシ樹脂の硬化剤、特に。 Conventionally, hardening agents for epoxy resins for electronic parts, especially.
プリント板用ソルダレストインクのエポキシ樹脂の硬化
剤には、特開昭６０−８２６７３号に開示されて、。A curing agent for epoxy resin in solder rest ink for printed boards is disclosed in Japanese Patent Application Laid-Open No. 60-82673.
いるように常温ではほとんど反応しない潜在性硬化剤に
属するジシアンジアミドとジアミノトリア。Dicyandiamide and diaminothoria belong to latent curing agents that hardly react at room temperature.
ジン誘導体が用いられている。Jin derivatives are used.
また、特開昭５９−１２６４２８号には、ジシアンジ。In addition, JP-A No. 59-126428 describes zithiandji.
アミドにモノエポキシ化合物を反応させて得られる液状
硬化剤が開示されている。A liquid curing agent obtained by reacting an amide with a monoepoxy compound is disclosed.
しかし１ジシアンジアミドとジアミノトリアジン誘導体
は共に粉末であるうえにエポキシ樹脂と。However, both dicyandiamide and diaminotriazine derivatives are powders and also contain epoxy resins.
の相溶性が悪く、らいかい機による混線とロール。poor compatibility, crosstalk and rolls caused by the laundering machine.
による混練を十分に行なう必要があるため作業性。Work efficiency is affected by the need for thorough mixing.
が悪く、かつ完全に均一な組成物を得ることが困。It is difficult to obtain a completely uniform composition.
難であった。It was difficult.
また、ジシアンジアミドとジアミノトリアジン誘導体は
、エポキシ樹脂を溶解する溶剤であるブチルセロソルブ
、カルピトール等には常温で溶解。In addition, dicyandiamide and diaminotriazine derivatives dissolve at room temperature in butyl cellosolve, calpitol, etc., which are solvents for dissolving epoxy resins.
度が極めて小さく、実質的にはほとんど溶解しな。Its concentration is extremely small, and it practically does not dissolve.
いという問題があった。 。There was a problem. .
一方、ジシアンジアミドにモノエポキシ化合物。On the other hand, dicyandiamide is a monoepoxy compound.
を反応させて得られる液状硬化剤は、常温で再結＋１
一晶し、この状態でソルダレジストの硬化剤に用いると
、スクリニン版の目づまりを起こし実用、に供。The liquid curing agent obtained by reacting the curable resin re-crystallizes +1 at room temperature, and if used as a curing agent for solder resist in this state, it will clog the screening plate and is not suitable for practical use.
し得ない問題があった。There was an unavoidable problem.
本発明の目的は上記した従来技術の問題点を解決し、均
一な混合状態が作業性良く得られるエボキシ樹脂用硬化
剤を提供するにある。An object of the present invention is to solve the above-mentioned problems of the prior art and to provide a curing agent for epoxy resin that can provide a uniform mixed state with good workability.
上記目的はジシアンジアミドと、ジアミノトリアジン誘
導体と、モノエポキシ化合物とを有機溶剤中で反応させ
て得られる常温で液状の化合物で一達成される。The above object is achieved by a compound that is liquid at room temperature and is obtained by reacting dicyandiamide, a diaminotriazine derivative, and a monoepoxy compound in an organic solvent.
即ち、上記目的はジシアンジアミド１モルに対してジア
ミノトリアジン誘導体を０．０５〜３モルと、モノエポ
キシ化合物０．５〜０．３モルと、有機溶剤を必要に応
じて適量配合しく好ましくはジシアンジアミド、ジアミ
ノトリアジン誘導体、モノエポキシ化合物の合計に対し
て２０〜４ｏ重量％配合）、。That is, the above object is achieved by blending 0.05 to 3 moles of a diaminotriazine derivative, 0.5 to 0.3 moles of a monoepoxy compound, and an appropriate amount of an organic solvent as necessary to 1 mole of dicyandiamide, preferably dicyandiamide, 20 to 4% by weight of the diaminotriazine derivative and monoepoxy compound).
８０〜１６０°Ｃで反応させて得られる常温で液状の司
ψ物により達成される。This is achieved using a substance that is liquid at room temperature and obtained by reaction at 80 to 160°C.
上記反応によりジシアンジアミド、並びにジアミノトリ
アジン誘導体の活性水素がモノエポキシ化合物の開環し
たエポキシ基が結合する。そしてジシアンジアミドとモ
ノエポキシ化合物との付加反応生成物ならびにジアミノ
トリアジン誘導体との付加反応生成物が共存することに
より硬化剤の。Through the above reaction, the active hydrogen of dicyandiamide and the diaminotriazine derivative is bonded to the ring-opened epoxy group of the monoepoxy compound. The addition reaction product of dicyandiamide and a monoepoxy compound and the addition reaction product of a diaminotriazine derivative coexist to form a curing agent.
液化が達成される。Liquefaction is achieved.
本発明で用いるジアミノトリアジン誘導体とし。 A diaminotriazine derivative used in the present invention.
ルイミダヅール（１’） ）エチルづ一トリアジン、イ
。Luimidazur (1') Ethyl triazine, I.
ソシアヌール酸付加物などがある。配合量はジシアンジ
アミド１モルに対して０．０５〜３．０モルがよく、好
ましくは０．１〜２０モルである。ジアミノトリアジン
誘導体が０．０５モルより少ないか、６．０モルより多
くなると未反応物などの析出が見られ、常温で均一な液
状硬化剤が得られない。These include socyanuric acid adducts. The blending amount is preferably 0.05 to 3.0 mol, preferably 0.1 to 20 mol, per 1 mol of dicyandiamide. If the amount of the diaminotriazine derivative is less than 0.05 mol or more than 6.0 mol, unreacted substances will precipitate, making it impossible to obtain a uniform liquid curing agent at room temperature.
本発明に用いるモノエポキシ化合物としては、アリルグ
リシジルエーテル、ブチルグリシジルエーテル、フェニ
ルグリシジルエーテル、オクチレ、 ３ 。Examples of the monoepoxy compound used in the present invention include allyl glycidyl ether, butyl glycidyl ether, phenyl glycidyl ether, and octyle.
ンオキサイド、ドデセンオキサイド、オレフィンオキサ
イド（好ましくはＣ１６〜Ｃ＋ｓのオレキンオフィ。dodecene oxide, olefin oxide (preferably C16 to C+s olefin oxide).
サイド）、スチレンオキサイド、Ｐ−ブチル７エ。side), styrene oxide, P-butyl 7e.
ノールグリシジルエーテル、タレジルグリシジルエーテ
ル、グリシジルメタクリレート、シクロへ。Norglycidyl ether, talesyl glycidyl ether, glycidyl methacrylate, to cyclo.
キセンビニルモノオキサイドなどである。配合量。Examples include xene vinyl monooxide. Mixed amount.
は用いるジシアンジアミドならびにジメチルトリ。used dicyandiamide and dimethyltri.
アジン誘導体それぞれ１モルに対して０．５〜３．０モ
。0.5 to 3.0 moles per mole of each azine derivative.
ルが好ましい。０．５モルより少ないと未反応物など。is preferred. If it is less than 0.5 mol, unreacted substances etc.
の析出が見られ常温で均一な液状硬化剤が得られない。Precipitation is observed, making it impossible to obtain a uniform liquid curing agent at room temperature.
一方３０モルより多いと、極めて高粘度の反応物が得ら
れ、多量の溶剤が必要なこと、ならびに主剤のエポキシ
樹脂と反応Ｔる残存活性水素が。On the other hand, if the amount is more than 30 moles, a reactant with extremely high viscosity will be obtained, requiring a large amount of solvent, and residual active hydrogen will react with the epoxy resin as the main ingredient.
減少するため、最終のエポキシ樹脂硬化物の物性が低下
し硬化剤として好ましくない。 １５本発明で
用いる溶剤としては、ソルダレジストのスクリーン印刷
性を考慮すれば、揮発性の小さい沸点が約１００°Ｃ以
上のものが使い易い。例えば。As a result, the physical properties of the final cured epoxy resin product deteriorate, making it undesirable as a curing agent. 15 As the solvent used in the present invention, a solvent with low volatility and a boiling point of about 100° C. or higher is easy to use, considering the screen printability of the solder resist. for example.
Ｌ−ブチルアルコール、メチルイソブチルカルピトール
、シクロヘキサノール、ループロピルアセ・ ４ ・
テート、ルーブチルアセテート、番ブチルアセテ。L-butyl alcohol, methylisobutylcarpitol, cyclohexanol, leupropylacetate, leubutyl acetate, butyl acetate.
、−）、、＄’ｇ（１’−ブチルアセテート、アミルア
セテ−。,-),, $'g (1'-butyl acetate, amyl acetate.
ト、メチルアミルアセテート、エチルラクテート、ブチ
ルラクテート、メチルオキシトールアセテ−。methylamyl acetate, ethyl lactate, butyl lactate, methyloxytol acetate.
ト、オキシトールアセテート、ブチルオキシド−５ルア
セテート、メチルジオキシトール、ジオキシ。t, oxytol acetate, butyl oxide-5-acetate, methyl dioxytol, dioxy.
トール、ブチルジオキシトール、メチル−ループ。toll, butyldioxytol, methyl-loop.
ロビルケトン、メチル−１ｓｏ−ブチルケトン、ジ。lobilketone, methyl-1so-butylketone, di.
イソブチルナトン、シクロヘキサノン、イソ７オ。Isobutylnaton, cyclohexanone, iso7o.
ロン、ジアセテートアルコール、ニトロメタン’１０ニ
トロエタン、エチレングリコールモノブチルエ。Ron, diacetate alcohol, nitromethane '10 nitroethane, ethylene glycol monobutyl ether.
−ｆル、エチレングリコールモノエチルエーテル。-fl, ethylene glycol monoethyl ether.
エチレングリコールモノエチルエーテルナトであ。Ethylene glycol monoethyl ether.
る。また、ソルダレジスト以外の用途に使用する５場合
には、アセトン、メチルエチルｔトンなど９゜低渉点溶
剤も用いられる。溶剤の配合量は原料主。Ru. Furthermore, when used for applications other than solder resists, solvents with a low 9° merging point such as acetone and methyl ethyl t-ton may also be used. The amount of solvent blended depends mainly on the raw materials.
成分（ジシアンジアミド、ジアミノトリアジン誘。Ingredients (dicyandiamide, diaminotriazine derivatives.
導体、モノエポキシ化合物）の２０〜４０重量％力５゜
取扱上好ましい。Conductor, monoepoxy compound) 20 to 40% by weight force 5° is preferred for handling.
本発明の硬化剤は、その使用にあたっては本汽７、−明
の硬化剤製造に使われたジシアンジアミドとジアミノト
リアジン誘導体の量を求め、従来処方り固体粉末を添加
）に使用していたジシアンジアミドとジアミノトリアジ
ン誘導体量に相当する量をベースに、モノエポキシを付
加反応させて減少す−る活性水素当量を計算により求め
、この分を補正して本硬化剤の添加量を決めることが望
ましい。When using the curing agent of the present invention, the amounts of dicyandiamide and diaminotriazine derivatives used in the production of the curing agent of Honki 7. It is desirable to determine the amount of active hydrogen equivalent that decreases by addition reaction of monoepoxy based on the amount corresponding to the amount of diaminotriazine derivative, and correct this amount to determine the amount of the curing agent added.
以下、本発明を具体的に実施例を挙げて説明する。Hereinafter, the present invention will be specifically explained with reference to Examples.
実施例１〜１２
カく拌機、温度計を備えた１ｔのセパラブルフラスコ中
に、ジシアンジアミド、ジアミノトリアジン誘導体、モ
ノエポキシ化合物、溶剤を全量で１００？仕込み、１２
０°Ｃオイルバス上で３０〜１２０ 分間加熱し、上記
両者を反応させた。ジシアンジアミドとジアミノトリア
ジン誘導体との配合割合、ジシアンジアミドとジアミノ
トリアジン誘導体に対するモノエポキシ化合物の配合割
合および溶剤の種類を第１表に示す。使用したジアミノ
トリアジン−ウンデシルイミダゾール−（１’） ）エ
チル−８−ト。Examples 1 to 12 In a 1 ton separable flask equipped with a stirrer and a thermometer, dicyandiamide, a diaminotriazine derivative, a monoepoxy compound, and a solvent were added in a total amount of 100 ml. Preparation, 12
The mixture was heated on a 0°C oil bath for 30 to 120 minutes to cause the two to react. Table 1 shows the blending ratio of dicyandiamide and diaminotriazine derivative, the blending ratio of monoepoxy compound to dicyandiamide and diaminotriazine derivative, and the type of solvent. Diaminotriazine-undecylimidazole-(1')ethyl-8-t used.
リアジン（以下Ｃで表わす） 、２．４−ジアミノ−６
゜（２′〜メチルイミダゾール（１ｒ、 ｌ エチル−
８−）す。Riazine (hereinafter referred to as C), 2,4-diamino-6
゜(2'~methylimidazole (1r, l ethyl-
8-).
アジン、インシアヌール酸付加物（以下ｄで表わ。Azine, incyanuric acid adduct (hereinafter represented by d).
す）である。また使用したモノエポキシ化合物は〉フェ
ニルグリシジルエーテル（以下ｅで表わす入）ブチルグ
リシジルエーテル（以下ｆで表わす）、タレジルグリシ
ジルエーテル（以下ｙで表わす）コＰ−ブチルフェノー
ルグリシジルエーテル（以下りで表わす）である。一方
溶剤の配装置は原料主成分（ジシアンジアミド、ジアミ
ノトリアジン誘導体、モノエポキシ化合物）の２０〜４
０重量％である。実施例１〜１２に示した反応生成物は
いずれも常温で均一な液体であり、長時間放置しても結
晶等の析出が見られず、極めて保存安定性が良い。). The monoepoxy compounds used were: phenyl glycidyl ether (hereinafter represented by e), butyl glycidyl ether (hereinafter represented by f), talesyl glycidyl ether (hereinafter represented by y), co-P-butylphenol glycidyl ether (hereinafter represented by It is. On the other hand, the solvent dispensing device is 20 to 4
It is 0% by weight. The reaction products shown in Examples 1 to 12 are all homogeneous liquids at room temperature, do not show precipitation of crystals even after being left for a long time, and have extremely good storage stability.
２（゛
・ ７ ・
・ ８ ・
実施例１〜１２で得られた硬化剤を用いてソルダ６レジ
ストインクを作り１硬化剤の特性を評価したρエポキシ
樹脂（溶化シェルエポキシ社製、エビコ。2 (゛・7・・8・Solder 6 resist ink was made using the curing agents obtained in Examples 1 to 12, and the properties of the curing agent 1 were evaluated.) ρ epoxy resin (manufactured by Solube Shell Epoxy Co., Ltd., Ebico).
−ト１５２ ） １００重量部、石英微粉末（龍森製、
５゜Ｘ）２０重量部、石英超微粉末（日本アエロジル社
８、゛製ＲＹ−２００’）３重量部、シリコーンオイル
（ト〒。-152) 100 parts by weight, fine quartz powder (manufactured by Tatsumori,
5°
レシリコーン社製、５Ｈ−２０３）２重量部、フタ。Manufactured by Resilicone, 5H-203) 2 parts by weight, lid.
ロシアニングリーン ２重量部にそれぞれ実施例。Example for each 2 parts by weight of Russianine Green.
１〜１２で得られた硬化剤を加え１２櫨類のツルダレ。Add the curing agent obtained in steps 1 to 12 and make a 12-cold vine.
シストインク２得た。硬化剤の添加量はエポキシ１゜樹
脂１００重量部に対して、硬化剤製造時に使われ。Cyst ink 2 was obtained. The amount of curing agent added is the amount used when manufacturing the curing agent per 100 parts by weight of epoxy 1° resin.
たジシアンジアミドとジアミノトリアジン誘導体。dicyandiamide and diaminotriazine derivatives.
量の和が１０重量部に相当する量とした。ガラスエ。The sum of the amounts was set to be equivalent to 10 parts by weight. Glasse.
ポキシ銅張り積層板にこれらのソルダレジストインクを
スクリーン印刷により塗布シ、１３ｏ０ｃ３ｏ筏。These solder resist inks were applied to a poxy copper-clad laminate by screen printing.
間加熱し硬化させた。なお印刷時には、スクリーン版の
目づまりは生じながった。ソルダレジスト硬化膜の特性
を第２表に示した。It was heated for a while to harden. Note that during printing, no clogging of the screen plate occurred. Table 2 shows the properties of the cured solder resist film.
なお１耐めっき性評価に用いためっき液の主成。Note 1: The main component of the plating solution used for plating resistance evaluation.
分は、次の通りである。The minutes are as follows.
実施列１〜１２の硬化剤を用いたソルダレジスト硬。Solder resist hardness using the hardening agents of Examples 1 to 12.
硬化膜は、いずれも絶縁抵抗、銅箔との密着性１０耐め
っき性へ半田耐熱性が良好であった。All of the cured films had good insulation resistance, adhesion to copper foil, plating resistance of 10, and soldering heat resistance.
以下余白 第 ２ 表 比較例１〜７ 比較のため、ジシアンジアミドとモノエポキシ化。Margin below Table 2 Comparative examples 1 to 7 For comparison, dicyandiamide and monoepoxidation.
合物との組合せ、ジアミノトリアジン誘導体とモノ。combination with compounds, diaminotriazine derivatives and mono.
エポキシ化合物との組合せ、およびジシアンジアミドと
ジアミノトリアジン誘導体とモノエポキシ、１１ 。Combinations with epoxy compounds and monoepoxies with dicyandiamide and diaminotriazine derivatives, 11.
化合物との組合せにおいて前２者のモル比が’６．０３
、 。In combination with the compound, the molar ratio of the former two is '6.03
, .
誓、の場合、前２者とモノエポキシのモル比が１４４の
。In the case of O, the molar ratio of the former two to monoepoxy is 144.
場合について、実施例、１〜１２に示したのと同じ手。For the cases, the same procedure as shown in Examples 1-12.
法を用いて、ジシアンジアミドならびにジアミノ。Dicyandiamide as well as diamino using the method.
トリアジン誘導体の液化を試みた（比較例１〜υ。An attempt was made to liquefy a triazine derivative (Comparative Examples 1 to υ).
反応温度は１２０〜１５９°０の範囲であり、１４０°
０以。The reaction temperature ranged from 120 to 159°0, and 140°
0 or more.
上で完全に溶解するものも一部あるが、いずれも。There are some that dissolve completely above, but none of them.
常温に戻すと第３表に示すように多量の粒子（結。When the temperature is returned to room temperature, a large amount of particles (condensation) appear as shown in Table 3.
晶）が析出し、均一な液状硬化剤が得られなかった。crystals) were precipitated, and a uniform liquid curing agent could not be obtained.
以下余白ＩＱ
・１２ ・
〔発明の効果〕
本発明によれば、固体粉末状のジシアンジアミドとジア
ミノトリアジン誘導体【常温で液状化することが可能と
なり、これをエポキシ樹脂系ソルダレジストインクの硬
化剤に用いると、スクリーン印刷による目づまりが起ら
ず、かつ粉末硬化剤が残存しない均一な塗膜が形成でき
１さらに硬化膜の特性も優れており、塗料等の被覆用の
エポキシ樹脂用硬化剤に有用である。The following margin IQ ・12 ・ [Effect of the invention] According to the present invention, solid powdered dicyandiamide and diaminotriazine derivative [can be liquefied at room temperature and used as a curing agent for epoxy resin solder resist ink] It is possible to form a uniform coating film that does not cause clogging due to screen printing and does not leave powder curing agent.1 Furthermore, the properties of the cured film are excellent, making it useful as a curing agent for epoxy resins used to coat paints, etc. be.
、１５ ・, 15・
Claims (1)
、モノエポキシ化合物とを反応させて得られる化合物か
らなるエポキシ樹脂硬化剤。1. An epoxy resin curing agent comprising a compound obtained by reacting dicyandiamide, a diaminotriazine derivative, and a monoepoxy compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3790987A JPH0655806B2 (en) | 1987-02-23 | 1987-02-23 | Curing agent for epoxy resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3790987A JPH0655806B2 (en) | 1987-02-23 | 1987-02-23 | Curing agent for epoxy resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63205313A true JPS63205313A (en) | 1988-08-24 |
| JPH0655806B2 JPH0655806B2 (en) | 1994-07-27 |
Family
ID=12510669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3790987A Expired - Lifetime JPH0655806B2 (en) | 1987-02-23 | 1987-02-23 | Curing agent for epoxy resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0655806B2 (en) |
Cited By (9)
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|---|---|---|---|---|
| EP0691802A1 (en) * | 1994-07-07 | 1996-01-10 | Morton International, Inc. | Method of forming a multilayer printed circuit board and product thereof |
| US5928839A (en) * | 1992-05-15 | 1999-07-27 | Morton International, Inc. | Method of forming a multilayer printed circuit board and product thereof |
| WO2012039380A1 (en) * | 2010-09-22 | 2012-03-29 | 積水化学工業株式会社 | Curable composition for inkjet and method for producing electronic component |
| WO2012039372A1 (en) * | 2010-09-24 | 2012-03-29 | 積水化学工業株式会社 | Curable composition for inkjet and method for producing electronic component |
| WO2012039379A1 (en) * | 2010-09-22 | 2012-03-29 | 積水化学工業株式会社 | Curable composition for inkjet, and method for producing electronic component |
| WO2012043473A1 (en) * | 2010-09-28 | 2012-04-05 | 積水化学工業株式会社 | Curable composition for inkjet applications, and process for manufacturing electronic component |
| JP2012087298A (en) * | 2010-09-24 | 2012-05-10 | Sekisui Chem Co Ltd | Inkjet curable composition and method of manufacturing electronic part |
| JPWO2012039372A1 (en) * | 2010-09-24 | 2014-02-03 | 積水化学工業株式会社 | Curable composition for inkjet and method for producing electronic component |
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-
1987
- 1987-02-23 JP JP3790987A patent/JPH0655806B2/en not_active Expired - Lifetime
Cited By (21)
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|---|---|---|---|---|
| US5928839A (en) * | 1992-05-15 | 1999-07-27 | Morton International, Inc. | Method of forming a multilayer printed circuit board and product thereof |
| EP0691802A1 (en) * | 1994-07-07 | 1996-01-10 | Morton International, Inc. | Method of forming a multilayer printed circuit board and product thereof |
| JPWO2012039380A1 (en) * | 2010-09-22 | 2014-02-03 | 積水化学工業株式会社 | Curable composition for inkjet and method for producing electronic component |
| WO2012039380A1 (en) * | 2010-09-22 | 2012-03-29 | 積水化学工業株式会社 | Curable composition for inkjet and method for producing electronic component |
| JP6066558B2 (en) * | 2010-09-22 | 2017-01-25 | 積水化学工業株式会社 | Curable composition for inkjet and method for producing electronic component |
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| US9249336B2 (en) | 2010-09-22 | 2016-02-02 | Sekisui Chemical Co., Ltd. | Curable composition for inkjet, and method for producing electronic component |
| JP2014159598A (en) * | 2010-09-22 | 2014-09-04 | Sekisui Chem Co Ltd | Curable composition for inkjet and method for producing electronic component |
| JPWO2012039379A1 (en) * | 2010-09-22 | 2014-02-03 | 積水化学工業株式会社 | Curable composition for inkjet and method for producing electronic component |
| JP5965642B2 (en) * | 2010-09-24 | 2016-08-10 | 積水化学工業株式会社 | Curable composition for inkjet and method for producing electronic component |
| JPWO2012039372A1 (en) * | 2010-09-24 | 2014-02-03 | 積水化学工業株式会社 | Curable composition for inkjet and method for producing electronic component |
| JP2015004063A (en) * | 2010-09-24 | 2015-01-08 | 積水化学工業株式会社 | Curable composition for inkjet and method for manufacturing electronic component |
| JP2012136681A (en) * | 2010-09-24 | 2012-07-19 | Sekisui Chem Co Ltd | Curable composition for inkjet, and method for producing printed wiring board |
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| JPWO2012043473A1 (en) * | 2010-09-28 | 2014-02-06 | 積水化学工業株式会社 | Curable composition for inkjet and method for producing electronic component |
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| JP6066559B2 (en) * | 2010-09-28 | 2017-01-25 | 積水化学工業株式会社 | Curable composition for inkjet and method for producing electronic component |
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Also Published As
| Publication number | Publication date |
|---|---|
| JPH0655806B2 (en) | 1994-07-27 |
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