JPWO2020095995A1 - 硬化性樹脂組成物 - Google Patents
硬化性樹脂組成物 Download PDFInfo
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- JPWO2020095995A1 JPWO2020095995A1 JP2020555583A JP2020555583A JPWO2020095995A1 JP WO2020095995 A1 JPWO2020095995 A1 JP WO2020095995A1 JP 2020555583 A JP2020555583 A JP 2020555583A JP 2020555583 A JP2020555583 A JP 2020555583A JP WO2020095995 A1 JPWO2020095995 A1 JP WO2020095995A1
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- 239000011342 resin composition Substances 0.000 title claims abstract description 45
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000000463 material Substances 0.000 claims abstract description 38
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- 239000006085 branching agent Substances 0.000 claims abstract description 16
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- 238000005304 joining Methods 0.000 claims abstract description 9
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
- -1 polytetramethylene Polymers 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 229920001971 elastomer Polymers 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 20
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- 239000002994 raw material Substances 0.000 description 5
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Classifications
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- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Description
すなわち、本発明における(C)ブロックウレタンは、(C−1)ポリイソシアネート、(C−2)ジオール、(C−3)イソシアネート基と反応する基を少なくとも3つ含む分岐剤からなる末端イソシアネート基を有するウレタンポリマーの末端イソシアネート基を、(C−4)ブロック剤でブロックした構造を有するものである。
上記アルキレンオキサイドを付加させた化合物は、市販品を使用してもよく、例えば、(株)ADEKA製のアデカポリエーテルシリーズである、AM−302、AM−502、AM−702、GM−30、GR−2505、GR−3308、G−300、G−400、G−700、G−1500、G−3000B、G−4000、T−400などが挙げられる。
実施例で使用した原料は以下の通りである。
(C−1)成分
IPDI:イソホロンジイソシアネート
HDI:ヘキサメチレンジイソシアネート
(C−2)成分
PTMG−2000:ポリテトラメチレングリコール(数平均分子量2000、三菱ケミカル(株)製)
(C−3)成分
G−3000B:グリセリンのプロピレンオキサイド付加物(数平均分子量3000、(株)ADEKA製)
TMP:トリメチロールプロパン
Boltorn H−2004:水酸基を6つ有する数平均分子量3200の化合物、Perstorp社製
G−700:グリセリンのプロピレンオキサイド付加物(数平均分子量700、(株)ADEKA製)
ソルビトール
(C−4)成分
PTBP:p−tert−ブチルフェノール
PCP:p−クミルフェノール(Sasol社製)
PMP:p−メトキシフェノール(東京化成工業(株)製)
(A)成分
EP−4100E:ビスフェノールA型エポキシ樹脂(エポキシ当量:190g/eq.、(株)ADEKA製)
(B)成分
EPR−1630:ゴム変性エポキシ樹脂(エポキシ当量:900g/eq.、(株)ADEKA製)
(D)成分
DICY:ジシアンジアミド
Fenuron:3−フェニル−1,1−ジメチルウレア
その他の成分
RY−200S:疎水性ヒュームドシリカ(日本アエロジル(株)製)
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−3)成分としてTMPを3.96g(水酸基モル数:0.089モル)、(C−1)成分としてIPDIを68.2g(イソシアネート基モル数:0.612モル)加え、100〜110℃で3時間反応させた。NCO%が2.45質量%であることを確認して、(C−4)成分としてPTBPを32.6g(0.217モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−1を得た。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−3)成分としてBoltorn H−2004を27.0g(水酸基モル数:0.054モル)、(C−1)成分としてHDIを51.5g(イソシアネート基モル数:0.612モル)加え、100〜110℃で3時間反応させた。NCO%が2.79質量%であることを確認して、(C−4)成分としてPTBPを37.8g(0.252モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−2を得た。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−3)成分としてソルビトールを1.7g(水酸基モル数:0.054モル)、(C−1)成分としてHDIを51.5g(イソシアネート基モル数:0.612モル)加え、100〜110℃で3時間反応させた。NCO%が2.99質量%であることを確認して、(C−4)成分としてPTBPを37.8g(0.252モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−3を得た。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−3)成分としてTMPを9.47g(水酸基モル数:0.212モル)、(C−1)成分としてHDIを56.6g(イソシアネート基モル数:0.673モル)加え、100〜110℃で3時間反応させた。NCO%が1.78質量%であることを確認して、(C−4)成分としてPTBPを23.3g(0.155モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−4を得た。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−3)成分としてTMPを5.2g(水酸基モル数:0.116モル)、(C−1)成分としてIPDIを68.2g(イソシアネート基モル数:0.612モル)加え、100〜110℃で3時間反応させた。NCO%が2.13質量%であることを確認して、(C−4)成分としてPTBPを28.5g(0.190モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−5を得た。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−3)成分としてTMPを0.7g(水酸基モル数:0.016モル)、(C−1)成分としてHDIを42.0g(イソシアネート基モル数:0.499モル)加え、100〜110℃で3時間反応させた。NCO%が2.17質量%であることを確認して、(C−4)成分としてPTBPを26.7g(0.178モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−6を得た。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−3)成分としてG−700を29.9g(水酸基モル数:0.119モル)、(C−1)成分としてIPDIを68.5g(イソシアネート基モル数:0.615モル)加え、100〜110℃で3時間反応させた。NCO%が2.17質量%であることを確認して、(C−4)成分としてPTBPを28.5g(0.190モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−7を得た。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−3)成分としてG−700を4.1g(水酸基モル数:0.016モル)、(C−1)成分としてIPDIを61.0g(イソシアネート基モル数:0.547モル)加え、100〜110℃で3時間反応させた。NCO%が2.17質量%であることを確認して、(C−4)成分としてPCPを47.9g(0.225モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−8を得た。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−3)成分としてG−700を29.9g(水酸基モル数:0.119モル)、(C−1)成分としてIPDIを68.5g(イソシアネート基モル数:0.615モル)加え、100〜110℃で3時間反応させた。NCO%が2.17質量%であることを確認して、(C−4)成分としてPMPを23.5g(0.190モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−9を得た。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−3)成分としてG−3000Bを300.0g(水酸基モル数:0.294モル)、(C−1)成分としてIPDIを66.4g(イソシアネート基モル数:0.596モル)加え、100〜110℃で3時間反応させた。NCO%が3.46質量%であることを確認して、(C−4)成分としてPTBPを45.4g(0.302モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−10を得た。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−1)成分としてIPDIを68.2g(イソシアネート基モル数:0.612モル)加え、100〜110℃で3時間反応させた。NCO%が3.49質量%であることを確認して、(C−4)成分としてPTBPを46.0g(0.306モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−11を得た。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−1)成分としてIPDIを44.3g(イソシアネート基モル数:0.398モル)加え、100〜110℃で3時間反応させた。NCO%が1.12質量%であることを確認して、(C−4)成分としてPTBPを13.8g(0.092モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−12を得た。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−3)成分としてTMPを1.54g(水酸基モル数:0.034モル)、(C−1)成分としてHDIを51.5g(イソシアネート基モル数:0.612モル)加え、100〜110℃で3時間反応させた。NCO%が1.80質量%であることを確認して、(C−4)成分としてPTBPを40.9g(0.272モル)添加し、さらに90〜100℃で3時間反応させた。IR吸収スペクトルにてNCOの吸収が消失したことを確認して反応を終了させ、ブロックウレタンBU−13を得た。
本製造例における(C−1)成分中のイソシアネート基のモル数(NCO基数)と、(C−2)成分中の水酸基と(C−3)成分中のイソシアネート基と反応する基の合計のモル数(NCO反応基数)の比(NCO基数/NCO反応基数)は、1.8であった。
ジムロート、撹拌羽根、窒素ラインを装着した1Lの5つ口セパラブル丸底フラスコに、(C−2)成分としてPTMG−2000を300.0g(水酸基モル数:0.306モル)、(C−3)成分としてTMPを13.9g(水酸基モル数:0.310モル)、(C−1)成分としてIPDIを106.4g(イソシアネート基モル数:0.955モル)加え、100〜110℃で反応を開始した。しかしながら、反応途中で系内の粘度が上昇してしまい、撹拌羽根による撹拌がうまく行えず、その後のブロック化の反応も行うことができず、ブロックウレタンBU−14を製造することができなかった。
本製造例における分岐剤率({(C−2)成分中の水酸基と(C−3)成分中のイソシアネート基と反応する基を合わせた基のモル数中の、(C−3)成分中のイソシアネート基と反応する基のモル数の割合}×100(%))は、50.3%であった。
EP−4100Eを70g、ブロックウレタンBU−1を30g、DICYを7g、炭酸カルシウムを25g、Fenuronを1g、RY−200Sを1g、500mlディスポカップに加え、25℃で5分間、スパチュラで撹拌した後、遊星式攪拌機を使用して更に撹拌し、硬化性樹脂組成物を得た。得られた硬化性樹脂組成物について、弾性率、最大点伸度、T型剥離強度を下記の通り測定した。結果を表1に示す。
樹脂組成物を180℃、30分で硬化させた後、JIS K 7161−1に準拠した方法に従って試験片を作製し、弾性率、最大点伸度を測定した。構造材料接合用接着剤の用途においては、柔軟な物性が求められていることから、1000MPa以下であるものを良品とし、最大点伸度においては、10%以上のものを良品とした。
被着材として片側に鉄、もう一方にアルミを使用し、JIS K 6854−3に従い、樹脂組成物を180℃、30分で硬化させた後、80℃におけるT型剥離強度を測定した。
また、被着材として鉄を使用し、JIS K 6854−3に従い、樹脂組成物を180℃、30分で硬化させた後、−40℃におけるT型剥離強度を測定した。
ブロックウレタンを表1、表2に記載の通りに変えたこと以外は、実施例1と同様の操作を行い、硬化性樹脂組成物を得た。得られた硬化性樹脂組成物について、それぞれ弾性率、最大点伸度、T型剥離強度を測定した。結果を表1に示す。
EP−4100Eを60g、EPR−1630を10g、ブロックウレタンBU−5を30g、DICYを7g、炭酸カルシウムを25g、Fenuronを1g、RY−200Sを1g、500mlディスポカップに加え、25℃で5分間、スパチュラで撹拌した後、遊星式攪拌機を使用して更に撹拌し、それぞれ硬化性樹脂組成物を得た。得られた硬化性樹脂組成物について、弾性率、最大点伸度、T型剥離強度を下記の通り測定した。結果を表1に示す。
Claims (7)
- (A)エポキシ樹脂、(C)ブロックウレタン及び(D)アミン系潜在性硬化剤を含む硬化性樹脂組成物であって、
(C)ブロックウレタンが、(C−1)ポリイソシアネート、(C−2)ジオール、(C−3)イソシアネート基と反応する基を少なくとも3つ含む分岐剤を反応させて得られる末端イソシアネート基を有するウレタンポリマーに、(C−4)ブロック剤を反応させることによって得られるものであり、
(C−1)成分中のイソシアネート基のモル数(NCO基数)と、(C−2)成分中の水酸基と(C−3)成分中のイソシアネート基と反応する基の合計のモル数(NCO反応基数)の比(NCO基数/NCO反応基数)が1.2以上1.8未満であり、
(C−2)成分中の水酸基と(C−3)成分中のイソシアネート基と反応する基の合計のモル数中、(C−3)成分中のイソシアネート基と反応する基のモル数の割合が、1〜50%である硬化性樹脂組成物。 - (B)ゴム成分を含む、請求項1に記載の硬化性樹脂組成物。
- (C−2)ジオールが、水、若しくはプロピレングリコールを開始剤としたプロピレンオキサイド付加重合物、及びポリテトラメチレングリコールから選択される少なくとも1種である、請求項1又は2に記載の硬化性樹脂組成物。
- (C−3)成分が、水酸基を少なくとも3つ有する化合物である、請求項1〜3の何れか1項に記載の硬化性樹脂組成物。
- (C−3)成分が、グリセリンのプロピレンオキサイド付加物、及びトリメチロールプロパンのプロピレンオキサイド付加物から選択される少なくとも1種である、請求項1〜4の何れか1項に記載の硬化性樹脂組成物。
- 請求項1〜5の何れか1項に記載の硬化性樹脂組成物を含有する、構造材料接合用接着剤。
- 請求項1〜5の何れか1項に記載の硬化性樹脂組成物を硬化させた硬化物。
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