JP7475019B2 - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
- Publication number
- JP7475019B2 JP7475019B2 JP2017222680A JP2017222680A JP7475019B2 JP 7475019 B2 JP7475019 B2 JP 7475019B2 JP 2017222680 A JP2017222680 A JP 2017222680A JP 2017222680 A JP2017222680 A JP 2017222680A JP 7475019 B2 JP7475019 B2 JP 7475019B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- curable composition
- oxazolidine
- acid
- compounds
- 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.)
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- -1 ester compound Chemical class 0.000 claims description 129
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- 125000001931 aliphatic group Chemical group 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 22
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- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 8
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Description
〔1〕イソシアネート基含有ウレタンプレポリマーと式(1)で示すエステル化合物とポリ塩化ビニルとオキサゾリジン化合物を含有し、前記オキサゾリジン化合物がオキサゾリジン環を分子内に2~3つ有する化合物であり、
前記式(1)で示すエステル化合物の配合量が硬化性組成物全体の3~40質量%、前記オキサゾリジン化合物の配合量が前記イソシアネート基含有ウレタンプレポリマーのイソシアネート基1モルに対し前記オキサゾリジン化合物が加水分解して生成する2級アミノ基の活性水素が0.1~1モルであることを特徴とする熱硬化用の硬化性組成物。
〔2〕さらに、硬化促進触媒、可塑剤、安定剤、充填剤、揺変性付与剤、接着性向上剤、貯蔵安定性向上剤、着色剤および有機溶剤から選択される1種以上の添加剤を含有することを特徴とする〔1〕に記載の熱硬化用の硬化性組成物。
ポリ塩化ビニルやポリウレア化合物は一般的に凝集力が強く、これらの粒子(粉体)を硬化性組成物に配合し攪拌分散すると、硬化性組成物中にブツやダマが発生して外観が悪化することが多い。また、ポリ塩化ビニルやポリウレア化合物の分散が不十分であると硬化性組成物の揺変性も低下する場合がある。そのため、ポリ塩化ビニルやポリウレア化合物を式(1)で示すエステル化合物中に仕込み、必要に応じて加温しながら攪拌分散してポリ塩化ビニルやポリウレア化合物の分散体を作製することが好ましい。ポリウレア化合物の分散体はポリウレア化合物の合成と同時に分散させてもよい。ポリ塩化ビニルやポリウレア化合物の分散体を硬化性組成物に配合することでブツやダマの発生がなく外観が良好で揺変性に優れた硬化性組成物を得ることができる。
さらに、本発明の硬化性組成物は、熱硬化時の耐発泡性や耐軟化性に優れるから、熱硬化性組成物として使用することができる。なお、本発明において熱硬化性組成物とは、100℃以上で硬化させることが可能であり、熱硬化後に大きな物性低下(発泡や軟化)が生じない組成物である。
攪拌機、温度計、窒素シール管および加温・冷却装置付き反応容器に、窒素ガスを流しながら有機溶剤(エクソールD110、エクソンモービル社製)を47.0g、ポリオキシプロピレントリオール(PML-S3008、旭硝子社製、数平均分子量8,370、総不飽和度0.005meq/g)を800.0g仕込み、攪拌しながらイソホロンジイソシアネート(テグサジャパン社製、分子量222.2)を78.7g、反応触媒としてオクチル酸錫(日東化成社製)を0.1g仕込み、70~80℃に加温し反応させた。滴定によるイソシアネート基含有量が理論値1.85質量%以下となった時点で反応を終了し(実測値1.79質量%)、冷却してイソシアネート基含有ウレタンプレポリマーPU-1を合成した。イソシアネート基含有ウレタンプレポリマーPU-1は、25℃での粘度が8,780mPa・sであり、常温で液体であった。
攪拌機、温度計、窒素シール管、エステル管、加熱・冷却装置付き反応容器に、ジエタノールアミン(分子量105)を435.0gとトルエンを183.0g仕込み、攪拌しながらイソブチルアルデヒド(分子量72.1)を328.0g仕込み、窒素ガス気流下で110~150℃に加温し還流脱水反応を続け、副生する水(74.5g)を系外に取り出した。反応終了後、さらに減圧下(50~70hPa)で加熱し、トルエンと未反応のイソブチルアルデヒドを除去し、中間の反応生成物であるN-ヒドロキシエチル-2-イソプロピルオキサゾリジンを得た。
次いで、得られたN-ヒドロキシエチル-2-イソプロピルオキサゾリジン659.0gに、さらにヘキサメチレンジイソシアネート(分子量168)を348.0g加え、80℃で8時間加熱し、滴定による実測NCO含有量が0.0質量%になった時点で反応終点とし、分子内にオキサゾリジン環を2つ有するウレタン結合含有オキサゾリジン化合物O-1を得た。ウレタン結合含有オキサゾリジン化合物O-1は常温で液体であった。
ジフェニルメタンジイソシアネート100.0gをトリメリット酸トリス(2-エチルヘキシル)300.0g中に溶解した溶液と、n-ブチルアミン55.0gをトリメリット酸トリス(2-エチルヘキシル)320.0g中に溶解した溶液を常温において反応させてポリウレア化合物の分散ペーストP-1を得た。分散ペーストP-1は、ポリウレア化合物20質量%とトリメリット酸トリス(2-エチルヘキシル)80質量%からなる。
[調製例2]
ジフェニルメタンジイソシアネート100.0gをフタル酸ジイソデシル300.0g中に溶解した溶液と、n-ブチルアミン55.0gをフタル酸ジイソデシル320.0g中に溶解した溶液を常温において反応させてポリウレア化合物の分散ペーストP-2を得た。分散ペーストP-2は、ポリウレア化合物20質量%とフタル酸ジイソデシル80質量%からなる。
[調製例3]
ジフェニルメタンジイソシアネート100.0gをフタル酸ビス(2-エチルヘキシル)300.0g中に溶解した溶液と、n-ブチルアミン55.0gをフタル酸ビス(2-エチルヘキシル)320.0g中に溶解した溶液を常温において反応させてポリウレア化合物の分散ペーストP-3を得た。分散ペーストP-3は、ポリウレア化合物20質量%とフタル酸ビス(2-エチルヘキシル)80質量%からなる。
[調製例4]
ジフェニルメタンジイソシアネート100.0gをフタル酸ジイソノニル300.0g中に溶解した溶液と、n-ブチルアミン55.0gをフタル酸ジイソノニル320.0g中に溶解した溶液を常温において反応させてポリウレア化合物の分散ペーストP-4を得た。分散ペーストP-4は、ポリウレア化合物20質量%とフタル酸ジイソノニル80質量%からなる。
[調製例5]
ジフェニルメタンジイソシアネート100.0gをアジピン酸ジイソノニル300.0g中に溶解した溶液と、n-ブチルアミン55.0gをアジピン酸ジイソノニル320.0g中に溶解した溶液を常温において反応させてポリウレア化合物の分散ペーストP-5を得た。分散ペーストP-5は、ポリウレア化合物20質量%とアジピン酸ジイソノニル80質量%からなる。
加熱冷却装置および窒素シール管付き混練容器に、窒素気流下で、合成例1で得たイソシアネート基含有ウレタンプレポリマーPU-1を100.0g、トリメリット酸トリス(2-エチルヘキシル)を16.1g、予め90~100℃の乾燥器中で乾燥して含有水分量を0.05質量%以下にした重質炭酸カルシウム(ホワイトンB、白石カルシウム社製)を108.0g、調製例1で得たポリウレア化合物の分散ペーストP-1を105.6g、ポリ塩化ビニル(VESTOLIT E7031、VESTOLIT社製)を48.3g、塩ビ用安定剤(アデカスタブSC-308E、ADEKA社製)を1.4g仕込み、内容物が均一になるまで攪拌混合した。この時点でポリ塩化ビニルはプラスチックゾルになった。次に、アクリル化合物(アロニックスM211B、ビスフェノールAEO変性(nは約2)ジアクリレート、東亞合成社製)を13.2g、ヒンダートフェノール系酸化防止剤(イルガノックス1010、BASF社製)を1.4g、ヒンダートアミン系光安定剤(サノールLS-292、三共社製)を1.4g、合成例2で得たウレタン結合含有オキサゾリジン化合物O-1を8.6g仕込み、内容物が均一になるまで攪拌、混合した。次いで、鉄(III)アセチルアセトネートを0.02g、p-トルエンスルホニルイソシアネートを0.5g仕込み、内容物が均一になるまで攪拌、混合し、減圧脱泡し、容器に充填密封して、硬化性組成物(シーリング材組成物)を調製した。
[実施例2]
実施例1において、トリメリット酸トリス(2-エチルヘキシル)の替わりにフタル酸ジイソデシルを16.1g仕込み、ポリウレア化合物の分散ペーストP-1の替わりにポリウレア化合物の分散ペーストP-2を105.6g仕込んだ以外は同様の操作を行い、硬化性組成物(シーリング材組成物)を調製した。
[比較例1]
実施例1において、トリメリット酸トリス(2-エチルヘキシル)の替わりにフタル酸ビス(2-エチルヘキシル)を16.1g、ポリウレア化合物の分散ペーストP-1の替わりにポリウレア化合物の分散ペーストP-3を105.6g仕込んだ以外は同様の操作を行い、硬化性組成物(シーリング材組成物)を調製した。
[比較例2]
実施例1において、トリメリット酸トリス(2-エチルヘキシル)の替わりにフタル酸ジイソノニルを16.1g、ポリウレア化合物の分散ペーストP-1の替わりにポリウレア化合物の分散ペーストP-4を105.6g仕込んだ以外は同様の操作を行い、硬化性組成物(シーリング材組成物)を調製した。
[比較例3]
実施例1において、トリメリット酸トリス(2-エチルヘキシル)の替わりにアジピン酸ジイソノニルを16.1g、ポリウレア化合物の分散ペーストP-1の替わりにポリウレア化合物の分散ペーストP-5を105.6g仕込んだ以外は同様の操作を行い、硬化性組成物(シーリング材組成物)を調製した。
[耐発泡性]
アルマイトアルミの表面に硬化性組成物を幅5mm×高さ3mm×長さ100mmのビード状(断面は半楕円状)に打設した後、23℃50%RHで0.5時間、24時間または72時間養生し試験体とした。各養生後、180℃に設定したオーブンの中に試験体を45分間入れて熱硬化させた。熱硬化後、試験体を23℃50%RHで24時間静置した。硬化物の外観および内部の発泡状態を目視で観察し下記の評価を行った。内部の発泡状態の観察は、硬化物の高さ1.5mmの位置からカッターでスライスするように長手方向に切り、硬化物の断面を目視で行った。
○:硬化物の外観に膨れはなく、内部に発泡は認められない
△:硬化物の外観に膨れはないが、内部に多くの発泡が認められる
×:硬化物の外観に膨れがあり、内部に多くの発泡が認められる
[硬度]
アルマイトアルミの表面に硬化性組成物を幅5mm×高さ3mm×長さ100mmのビード状(断面は半楕円状)に打設した後、23℃50%RHで0.5時間、24時間または72時間養生し試験体とした。各養生後、180℃に設定したオーブンの中に試験体を45分間入れて熱硬化させた。熱硬化後、試験体を23℃50%RHで24時間静置した。硬化物(高さ3mmの箇所)の硬度をタイプAデュロメータで測定した。
常態養生を行い加熱養生しない場合、実施例1~2および比較例1~3の硬化性組成物の耐発泡性や耐軟化性は良好である。比較例1~3の硬化性組成物は、180℃の加熱養生(熱硬化時)において、熱の影響により発泡や硬度低下(軟化)が生じたと考えられる。
Claims (2)
- イソシアネート基含有ウレタンプレポリマーと式(1)で示すエステル化合物とポリ塩化ビニルとオキサゾリジン化合物を含有し、前記オキサゾリジン化合物がオキサゾリジン環を分子内に2~3つ有する化合物であり、
前記式(1)で示すエステル化合物の配合量が硬化性組成物全体の3~40質量%、前記オキサゾリジン化合物の配合量が前記イソシアネート基含有ウレタンプレポリマーのイソシアネート基1モルに対し前記オキサゾリジン化合物が加水分解して生成する2級アミノ基の活性水素が0.1~1モルであることを特徴とする熱硬化用の硬化性組成物。
- さらに、硬化促進触媒、可塑剤、安定剤、充填剤、揺変性付与剤、接着性向上剤、貯蔵安定性向上剤、着色剤および有機溶剤から選択される1種以上の添加剤を含有することを特徴とする請求項1に記載の熱硬化用の硬化性組成物。
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