JP6721855B2 - エポキシ樹脂組成物及び接着剤 - Google Patents
エポキシ樹脂組成物及び接着剤 Download PDFInfo
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- JP6721855B2 JP6721855B2 JP2015118329A JP2015118329A JP6721855B2 JP 6721855 B2 JP6721855 B2 JP 6721855B2 JP 2015118329 A JP2015118329 A JP 2015118329A JP 2015118329 A JP2015118329 A JP 2015118329A JP 6721855 B2 JP6721855 B2 JP 6721855B2
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- epoxy resin
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- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
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- 239000000539 dimer Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
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- BXDCELKJGGVUHD-UHFFFAOYSA-N ethyl(methyl)phosphane Chemical compound CCPC BXDCELKJGGVUHD-UHFFFAOYSA-N 0.000 description 1
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- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
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- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
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- 239000010410 layer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003562 lightweight material Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 description 1
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
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- 150000004780 naphthols Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
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- DBIWHDFLQHGOCS-UHFFFAOYSA-N piperidine;trifluoroborane Chemical compound FB(F)F.C1CCNCC1 DBIWHDFLQHGOCS-UHFFFAOYSA-N 0.000 description 1
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Landscapes
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- Adhesives Or Adhesive Processes (AREA)
Description
本発明のエポキシ樹脂組成物は、エポキシ当量が350〜700g/当量の範囲であるビスフェノール型又はビフェノール型エポキシ樹脂(A)と、ポリアルキレンオキサイド構造を有する2官能エポキシ樹脂(B)とを含有することを特徴とする。本発明では、ビスフェノール型又はビフェノール型エポキシ樹脂(A)と、ポリアルキレンオキサイド構造を有する2官能エポキシ樹脂(B)との2種のエポキシ樹脂を併用すること、前記エポキシ樹脂(A)のエポキシ当量が350〜700g/当量の範囲であることにより、硬化物における柔軟性と靱性とに非常に優れる効果を奏する。
の何れかで表される構造部位であり、nは1以上の整数である。]
で表されるものが挙げられる。これらはそれぞれ単独で用いても良いし、2種類以上を併用しても良い。
の何れかで表される化合物などが挙げられる。これらはそれぞれ単独で用いても良いし、2種類以上を併用しても良い。中でも、硬化物における柔軟性と靱性に優れることから、前記一般式(3−1)又は(3−2)で表される化合物が好ましい。
の何れかで表される構造部位である。R4は炭素原子数2〜6のアルキル基であり、mはそれぞれ独立に1以上の整数である。]
で表されるものなどが挙げられる。これらはそれぞれ単独で用いても良いし、2種類以上を併用しても良い。
温度計、攪拌器、及び還流冷却器を備えたフラスコに、窒素雰囲気下で、ビスフェノールA型エポキシ樹脂(DIC株式会社製「EPICLON 850」エポキシ当量188g/当量)を764質量部、ビスフェノールAを236質量部仕込み、80℃まで昇温した。触媒としてテトラメチルアンモニウムクロライドを0.03質量部添加したのち、140℃まで昇温し、同温度でエポキシ当量が501g/当量になるまで反応させて、ビスフェノール型エポキシ樹脂(A−1)を得た。
製造例1において、ビスフェノール型エポキシ樹脂とビスフェノールとの種類及び反応割合を表1に示す通り変更した以外は製造例1と同様にしてビスフェノール型エポキシ樹脂(A−2)〜(A−4)を得た。
前記製造例1で得たビスフェノール型エポキシ樹脂(A−1)1000質量部を100℃に加温し、ポリアルキレンオキサイド構造を有する2官能エポキシ樹脂(B−1)[新日本理化社製「リカレジンBEO−60E」、ビスフェノールAビス(トリエチレングリコールジグリシジルエーテル)エーテル、エポキシ当量351g/当量]を1000質量部仕込み混合し、エポキシ樹脂組成物(1)を得た。
表2に示す配合割合とした以外は実施例1と同様にしてエポキシ樹脂組成物(2)〜(4)を得た。
表2に示す配合割合とした以外は実施例1と同様にしてエポキシ樹脂組成物(1’)を得た。
硬化性組成物(I)の調整及び評価
実施例1〜4及び比較例1で得たエポキシ樹脂組成物を用いて、下記要領で硬化性組成物(I)を調整し、その硬化物について各種評価試験を行った。結果を表3に示す。
エポキシ樹脂組成物、2−エチル−4−メチルイミダゾール、及び3−(3,4−ジクロロフェニル)−N,N−ジメチル尿素を表3に示す割合で配合し、硬化性組成物(I)を得た。
先で得た硬化性組成物(I)を膜厚が2mmの金型に注入し、150℃で1時間かけて硬化させた。硬化物から1号ダンベル型のサンプルを切り出し、島津製作所株式会社製「AUTOGRAPH AG−IS 1kN」を用いて引張試験を行い、伸び率(%)で評価した。
先で得た硬化性組成物(I)を用い2枚の鋼板を熱硬化接着した。接着層の膜厚は0.2mmとし、150℃で1時間加熱し硬化させた。得られた接着試験鋼板について、JIS K6859(接着剤のクリープ破壊試験)に基づき、島津製作所株式会社製「AUTOGRAPH AG-IS 10kN」を用いて引張せん断試験を行い、破断強度(MPa)で評価した。
硬化性組成物(II)〜(IV)の調整及び評価
実施例1〜4で得たエポキシ樹脂組成物を用いて、下記要領で硬化性組成物(II)〜(IV)を調整し、その硬化物について各種評価試験を行った。結果を表4〜6に示す。
エポキシ樹脂組成物、ポリエーテルアミン(ハンツマン社製「JEFFAMINE D-230」活性水素当量57g/当量)を表4に示す割合で配合し、硬化性組成物(II)を得た。
先で得た硬化性組成物(II)を膜厚が2mmになるように金型に注入し、80℃、100℃、120℃で順に、それぞれ3時間ずつ加熱し硬化させた。硬化物から1号ダンベル型のサンプルを切り出し、島津製作所株式会社製「AUTOGRAPH AG−IS 1kN」を用いて引張試験を行い、伸び率(%)で評価した。
先で得た硬化性組成物(II)を用い2枚の鋼板を熱硬化接着した。接着層の膜厚は0.2mmとし、80℃、100℃、120℃で順に、それぞれ3時間ずつ加熱し硬化させた。得られた試験鋼板について、JIS K6859(接着剤のクリープ破壊試験)に基づき、島津製作所株式会社製「AUTOGRAPH AG-IS 10kN」を用いて引張せん断試験を行い、破断強度(MPa)で評価した。
エポキシ樹脂組成物、ジシアンジアミド、3,4−ジクロロフェニル−N,N−ジメチル尿素を表5に示す割合で配合し、硬化性組成物(III)を得た。
先で得た硬化性組成物(III)を膜厚が2mmになるように金型に注入し、180℃で1時間加熱し硬化させた。硬化物から1号ダンベル型のサンプルを切り出し、島津製作所株式会社製「AUTOGRAPH AG−IS 1kN」を用いて引張試験を行い、伸び率(%)で評価した。
先で得た硬化性組成物(III)用い2枚の鋼板を熱硬化接着した。接着層の膜厚は0.2mmとし、180℃で1時間加熱し硬化させた。得られた接着試験鋼板について、JIS K6859(接着剤のクリープ破壊試験)に基づき、島津製作所株式会社製「AUTOGRAPH AG-IS 10kN」を用いて引張せん断試験を行い、破断強度(MPa)で評価した。
エポキシ樹脂組成物、アミド樹脂(DIC株式社製「ラッカマイド TD−960」活性水素当量78g/当量)を表6に示す割合で配合し、硬化性組成物(IV)を得た。
先で得た硬化性組成物(IV)を膜厚が2mmになるように金型に注入し、80℃、100℃、120℃で順に、それぞれ3時間ずつ加熱し硬化させた。硬化物から1号ダンベル型のサンプルを切り出し、島津製作所株式会社製「AUTOGRAPH AG−IS 1kN」を用いて引張試験を行い、伸び率(%)で評価した。
先で得た硬化性組成物(IV)用い2枚の鋼板を熱硬化接着した。接着層の膜厚は0.2mmとし、80℃、100℃、120℃で順に、それぞれ3時間ずつ加熱し硬化させた。得られた接着試験鋼板について、JIS K6859(接着剤のクリープ破壊試験)に基づき、島津製作所株式会社製「AUTOGRAPH AG-IS 10kN」を用いて引張せん断試験を行い、破断強度(MPa)で評価した。
Claims (8)
- エポキシ当量が350〜700g/当量の範囲である、下記構造式(1)
の何れかで表される構造部位であり、nは1以上の整数である。]
で表されるビスフェノール型又はビフェノール型エポキシ樹脂(A)と、
下記構造式(4)
の何れかで表される構造部位である。R4は炭素原子数2〜6のアルキル基であり、mはそれぞれ独立に1以上の整数である。]
で表される、エポキシ当量が250〜550g/当量の範囲であるポリアルキレンオキサイド構造を有する2官能エポキシ樹脂(B)と、を含有し、
質量比[(A)/(B)]が30/70〜70/30の範囲となる割合で両者を含有することを特徴とするエポキシ樹脂組成物。 - 前記構造式(4)中のYが前記(5−1)又は(5−2)で表される構造部位である請求項1記載のエポキシ樹脂組成物。
- 前記構造式(4)中のmがそれぞれ1〜6の整数であり、かつ構造式中2つのmの合計が2〜12の範囲である請求項1又は2記載のエポキシ樹脂組成物。
- エポキシ当量が300〜600g/当量の範囲である請求項1〜3の何れか1項記載のエポキシ樹脂組成物。
- 請求項1〜4の何れか一つに記載のエポキシ樹脂組成物と、硬化剤又は硬化促進剤とを含有する硬化性組成物。
- 前記硬化剤又は硬化促進剤がイミダゾール化合物、ポリエーテルアミン化合物、アミド化合物の何れかである請求項5記載の硬化性組成物。
- 請求項5又は6記載の硬化性組成物を硬化させて得られる硬化物。
- 請求項1〜4の何れか一つに記載のエポキシ樹脂組成物と、硬化剤又は硬化促進剤とを含有する接着剤。
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