JP2022515712A - 低い硬化温度及び良好な貯蔵安定性を有する熱硬化性エポキシ樹脂組成物 - Google Patents
低い硬化温度及び良好な貯蔵安定性を有する熱硬化性エポキシ樹脂組成物 Download PDFInfo
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
Description
(a)1分子あたり平均1つを超えるエポキシ基を有する少なくとも一つのエポキシ樹脂A;
(b)グルタル酸ジヒドラジド、アジピン酸ジヒドラジド、及びピメリン酸ジヒドラジド、好ましくはアジピン酸ジヒドラジド、からなる群から選択されるジヒドラジドであるエポキシ樹脂のための少なくとも一つの硬化剤B;及び
(c)式(Ia)又は(Ib)の少なくとも一つの促進剤C:
R2及びR3は、それぞれ独立して、アルキル基又はアラルキル基であるか;あるいは一緒になって、3~20の炭素原子を有し、かつ5~8つ、好ましくは6つの環原子を有する任意選択的に置換された複素環の一部分である二価の脂肪族基であるかのいずれかであり;
R1’は、n’価の脂肪族、脂環式、又は芳香脂肪族基であり;
R2’は、アルキル基、又はアラルキル基、又はアルキレン基であり;
R3’は、独立して、H又はアルキル基若しくはアラルキル基であり;かつ
n及びn’は、それぞれ1~4、特に1又は2の値を有する)。
(c)下記の式(Ia)又は(Ib)の少なくとも一つの促進剤Cをさらに含む:
R2及びR3は、それぞれ独立して、アルキル基又はアラルキル基であるか;あるいは一緒になって、3~20の炭素原子を有し、かつ5~8つ、好ましくは6つの環原子を有する任意選択的に置換された複素環の一部分である二価の脂肪族基であるかのいずれかであり;
R1’は、n’価の脂肪族、脂環式、又は芳香脂肪族基であり;
R2’は、アルキル基、又はアラルキル基、又はアルキレン基であり;
R3’は、独立して、H又はアルキル基若しくはアラルキル基であり;かつ
n及びn’は、それぞれ1~4、特に1又は2の値を有する)。
R1[NCO]n (III)
4~10の炭素原子を有するアルキレン基、特にヘキサメチレン基、又は
イソシアネート基の除去後の脂肪族若しくは芳香脂肪族ジイソシアネートのビウレット若しくはイソシアヌレート;又は
キシリレン基、特にm-キシリレン基
である。
- R1は、Hであり、且つR2及びR3は、それぞれメチル、エチル又はプロピル基であり、好ましくはそれぞれメチル基であり、且つn=1であり、及び/又は
- R1は、
エポキシ樹脂組成物の全重量に基づいて、
10~60重量%、特に20~30重量%の強靭性向上剤D1;
10~30重量%、特に20~30重量%の強靭性向上剤D2;
10~30重量%、特に20~30重量%の強靭性向上剤D3。
- 一官能価の飽和又は不飽和、分枝又は非分枝、環式又は開鎖C4~C30アルコールのグリシジルエーテル、例えばブタノールグリシジルエーテル、ヘキサノールグリシジルエーテル、2-エチルヘキサノールグリシジルエーテル、アリルグリシジルエーテル、テトラヒドロフルフリル及びフルフリルグリシジルエーテル、トリメトキシシリルグリシジルエーテルなど;
- 二官能価の飽和又は不飽和、分枝又は非分枝、環式又は開鎖C2~C30アルコールのグリシジルエーテル、例えばエチレングリコールグリシジルエーテル、ブタンジオールグリシジルエーテル、ヘキサンジオールグリシジルエーテル、オクタンジオールグリシジルエーテル、シクロヘキサンジメタノールジグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテルなど;
- 三又は多官能価の飽和又は不飽和、分枝又は非分枝、環式又は開鎖アルコールのグリシジルエーテル、例えばエポキシドヒマシ油、エポキシドトリメチロールプロパン、エポキシドペンタエリスリトール又はソルビトール、グリセロール、トリメチロールプロパンなどの脂肪族ポリオールのポリグリシジルエーテルなど;
- フェノール化合物及びアニリン化合物のグリシジルエーテル、例えばフェニルグリシジルエーテル、クレジルグリシジルエーテル、p-tert-ブチルフェニルグリシジルエーテル、ノニルフェノールグリシジルエーテル、3-n-ペンタデセニルグリシジルエーテル(カシューナット油由来)、N,N-ジグリシジルアニリンなど;
- エポキシドアミン、例えばN,N-ジグリシジルシクロヘキシルアミンなど;
- エポキシドモノ又はジカルボン酸、例えばグリシジルネオデカノエート、グリシジルメタクリレート、グリシジルベンゾエート、グリシジルフタレート、テトラヒドロフタレート及びヘキサヒドロフタレート、二量体脂肪酸のジグリシジルエステルなど;
- エポキシド二又は三官能価の低分子量~高分子量のポリエーテルポリオール、例えばポリエチレングリコールグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテルなど。
- エポキシ樹脂組成物の全重量に基づいて10~60重量%、特に30~50重量%の、1分子あたり平均1つを超えるエポキシ基を有するエポキシ樹脂A;好ましくは、エポキシ樹脂Aの50~100重量%、特に80~100重量%は、液体エポキシ樹脂であり、且つエポキシ樹脂Aの0~30重量%、特に0~20重量%、より好ましくは5~15重量%は、固体エポキシ樹脂である;
- 硬化剤B、好ましくはアジピン酸ジヒドラジド;
- 式(Ia)又は(Ib)の少なくとも1つ、特に式(Ia)の促進剤Cであって、式中、特に、
- R1は、Hであり、且つR2及びR3は、それぞれメチル、エチル又はプロピル基であり、好ましくはそれぞれメチル基であり、且つn=1であり、及び/又は
- R1は、
- 好ましくは、末端ブロックポリウレタンポリマーD1、液体ゴムD2、及びコア-シェルポリマーD3からなる群から選択される少なくとも1つの強靭性向上剤Dであって、その割合は、エポキシ樹脂組成物の全重量に基づいて、以下:
強靭性向上剤D1 10~60重量%、特に20~30重量%;
強靭性向上剤D2 10~30重量%、特に20~30重量%;
強靭性向上剤D3 10~30重量%、特に20~30重量%
の通りである、少なくとも1つの強靭性向上剤D;
- エポキシ樹脂組成物の全重量に基づいて、好ましくは5~50重量%、好ましくは10~30重量%の、炭酸カルシウム、酸化カルシウム及びヒュームドシリカからなる群から選択される充填剤F;
- エポキシ樹脂組成物の全重量に基づいて、好ましくは0.1~15重量%、好ましくは0.1~5重量%、特に好ましくは0.1~2重量%、より好ましくは0.2~1重量%のエポキシ含有反応性希釈剤G。
(i)上記で詳細に説明された熱硬化性エポキシ樹脂組成物を熱安定性基材S1の表面、特に金属の表面に適用すること;
(ii)適用した熱硬化性エポキシ樹脂組成物を、さらなる熱安定性基材S2の表面、特に金属の表面に接触させること;
(iii)100~220℃、特に120~200℃、好ましくは130~150℃、より好ましくは130~140℃の温度まで組成物を加熱すること。
150gのpoly-THF2000(OH価57mg/g KOH)及び150gのLiquiflex H(OH価46mg/g KOH)を30分間、105℃において減圧下で乾燥させた。温度が90℃まで減少したら、61.5gのIPDI及び0.14gのジブチルスズジラウレートを添加した。2.0時間後、NCO含有量が3.10%で一定になるまで、反応を90℃において減圧下で実施した(算出されたNCO含有量:3.15%)。その後、96.1gのカルダノールを遮断剤として添加した。いずれの遊離NCOも検出不可能となるまで、105℃の減圧下において撹拌を続けた。この生成物を強靭性向上剤D-1として使用した。
参照組成物R1~R8及び本発明の組成物E1~E8は、表1の数字に従って製造された。表1中の規定された量は、重量部である。
弾性率(DIN EN ISO 527)
接着剤試料を2つのテフロン(登録商標)紙間で2mmの層厚さまで押圧した。175℃で35分間硬化させた後、テフロン(登録商標)紙を取り出し、且つ試験片をDIN標準状態に型抜きした。2mm/分の負荷速度において標準気象条件で試験片を試験した。DIN EN ISO 527により、0.05~0.25%の弾性率を決定した。
Anticorit PL 3802-39Sで再び油処理されたElo H420鋼(厚さ1.5mm)のクリーニングされた試験片を、0.3mmの層厚でスペーサーとしてガラスビーズを用いて25×10mmの結合領域上で接着剤によって結合させ、且つ10分間、オーブン温度140℃で硬化した。
接着剤及び90×20×0.8mmの寸法を有するDC04+ZE鋼を用いて試験片を製造した。ここで、接着領域は、スペーサーとしてガラスビーズを用いて0.3mmの層厚で20×30mmであった。10分間、オーブン温度140℃で試料を硬化した。衝撃剥離強度は、23℃において、三重決定としてZwick 450衝撃振子上で測定した。報告された衝撃剥離強度は、ISO 11343への25%から90%までの測定曲線下でのN/mmでの平均力である。
以下のパラメーター:5Hz、1mm間隔、プレート直径25mm、1%変形を用いて、25℃の温度においてプレート-プレート配列を使用する振動により、Anton Paar MCR 101レオメーター上において、製造から1日後に接着剤の粘度測定を実行した。測定は、表2では「Visco初期25℃」で示される。
Claims (14)
- 以下を含む熱硬化性エポキシ樹脂組成物:
(a)1分子あたり平均1つを超えるエポキシ基を有する少なくとも一つのエポキシ樹脂A;
(b)グルタル酸ジヒドラジド、アジピン酸ジヒドラジド、及びピメリン酸ジヒドラジド、好ましくはアジピン酸ジヒドラジド、からなる群から選択されるジヒドラジドであるエポキシ樹脂のための少なくとも一つの硬化剤B;及び
(c)下記の式(Ia)又は(Ib)の少なくとも一つの促進剤C:
R1は、H又はn価の脂肪族、脂環式、若しくは芳香脂肪族基であり;
R2及びR3は、それぞれ独立して、アルキル基又はアラルキル基であるか;あるいは一緒になって、3~20の炭素原子を有し、かつ5~8つ、好ましくは6つの環原子を有する任意選択的に置換された複素環の一部分である二価の脂肪族基であるかのいずれかであり;
R1’は、n’価の脂肪族、脂環式又は芳香脂肪族基であり;
R2’は、アルキル基、又はアラルキル基、又はアルキレン基であり;
R3’は、独立して、H又はアルキル基若しくはアラルキル基であり;かつ
n及びn’は、それぞれ1~4、特に1又は2の値を有する)。 - R1は、Hであり、かつR2及びR3は、それぞれメチル、エチル、又はプロピル基、好ましくはそれぞれメチル基であり、かつn=1であることを特徴とする、請求項1に記載の熱硬化性エポキシ樹脂組成物。
- モルでの前記エポキシ樹脂Aのエポキシ基の割合/モルでのジヒドラジドの割合の比率は、3~5、特に3.5~4.5であることを特徴とする、請求項1~3のいずれか一項に記載の熱硬化性エポキシ樹脂組成物。
- 前記ジヒドラジドは、≦100μm、≦50μm、0.5~50μm、1~50μm、1~40μm、特に1~20μm、好ましくは2~20μm、特に好ましくは2~15μmのメジアン粒径D50を有することを特徴とする、請求項1~4のいずれか一項に記載の熱硬化性エポキシ樹脂組成物。
- 前記熱硬化性エポキシ樹脂組成物の全重量に基づいて、0.5重量%未満、好ましくは0.3重量%未満、最も好ましくは0.1重量%未満のジシアンジアミドを含むことを特徴とする、請求項1~5のいずれか一項に記載の熱硬化性エポキシ樹脂組成物。
- 前記エポキシ樹脂Aのエポキシ基1モルあたりのグラムでの促進剤Cの割合の比率は、0.01~0.5g/エポキシ基1モル、特に0.05~0.3g/エポキシ基1モル、より好ましくは0.075~0.2g/エポキシ基1モル、最も好ましくは0.08~0.15g/エポキシ基1モルであることを特徴とする、請求項1~6のいずれか一項に記載の熱硬化性エポキシ樹脂組成物。
- 末端ブロックポリウレタンポリマーD1、液体ゴムD2、及びコア-シェルポリマーD3、好ましくは末端ブロックポリウレタンポリマーD1、からなる群から選択される少なくとも一つの強靭性向上剤Dを追加的に含むことを特徴とする、請求項1~7のいずれか一項に記載の熱硬化性エポキシ樹脂組成物。
- 前記エポキシ樹脂Aの割合は、前記熱硬化性エポキシ樹脂組成物の全重量に基づいて、10~60重量%、特に30~50重量%であることを特徴とする、請求項1~8のいずれか一項に記載の熱硬化性エポキシ樹脂組成物。
- 25℃において500~3000Pa・s、特に1000~2500Pa・s、好ましくは1000~2000Pa・sの粘度を有することを特徴とする、請求項1~9のいずれか一項に記載の熱硬化性エポキシ樹脂組成物。
- 一成分熱硬化性接着剤、特に動力車構造における熱硬化性一成分車体接着剤としての、請求項1~10のいずれか一項に記載の熱硬化性エポキシ樹脂組成物の使用。
- 以下を含む、熱安定性基材を接着結合するための方法:
(i)請求項1~10のいずれか一項に記載の熱硬化性エポキシ樹脂組成物を熱安定性基材S1の表面、特に金属の表面に適用すること;
(ii)適用した前記熱硬化性エポキシ樹脂組成物を、さらなる熱安定性基材S2の表面、特に金属の表面に接触させること;
(iii)100~220℃、特に120~200℃、好ましくは130~150℃、より好ましくは130~140℃の温度まで前記組成物を加熱すること;
ここで、前記基材S2は、前記基材S1と同一の材料、又は前記基材S1と異なる材料からなる。 - 100~220℃、特に120~200℃、好ましくは130~150℃、より好ましくは130~140℃の温度まで前記組成物を加熱する工程(iii)において、前記組成物は、前記温度に10分~6時間、10分~2時間、10分~60分、10分~30分、10分~20分、より好ましくは10分~15分にわたって保持される、請求項12に記載の方法。
- 請求項12又は13に記載の方法から得られる接着結合された物品。
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