JP2020516756A - 自己修復性ポリウレタン系重合体およびその製造方法 - Google Patents
自己修復性ポリウレタン系重合体およびその製造方法 Download PDFInfo
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Abstract
Description
[関係式1]
0.1≦M[disulfide]/M[OH]
(前記関係式1中、M[disulfide]は、組成物中の芳香族ジスルフィドジオールの合計モル数であり、M[OH]は、組成物中の芳香族ジスルフィドジオールおよびポリオールの合計モル数である。)
[関係式2]
50≦T1/T0×100
(前記関係式2中、T0は、自己修復性ポリウレタン系重合体の切断前の靭性(MJ/m3)であり、T1は、自己修復性ポリウレタン系重合体を切断し、25℃の温度条件で2時間再接合した後の靭性(MJ/m3)である。)
[関係式3]
0.15≦M[cycloaliphatic]/M[NCO]≦1
(前記関係式1中、M[cycloaliphatic]は、組成物中の脂環族ポリイソシアネートの合計モル数であり、M[NCO]は、組成物中のポリイソシアネート系化合物の合計モル数である。)
50≦T1/T0×100
(前記関係式2中、T0は、自己修復性ポリウレタン系重合体の切断前の靭性(MJ/m3)であり、T1は、自己修復性ポリウレタン系重合体を切断し、25℃の温度条件で2時間再接合した後の靭性(MJ/m3)である。)
0.1≦M[disulfide]/M[OH]
0.15≦M[cycloaliphatic]/M[NCO]≦1
(前記関係式1中、M[cycloaliphatic]は、組成物中の脂環族ポリイソシアネートの合計モル数であり、M[NCO]は、組成物中のポリイソシアネート系化合物の合計モル数である。)
機械式撹拌機、温度計が取り付けられた0.5Lの三つ口フラスコにポリテトラメチレンエーテルグリコール(PTMEG、14.5mmol、14.5g、数平均分子量1,000g/mol、コリアPTG社製)を投入した後、100℃で真空乾燥し、水分を除去した。その後、70℃でイソホロンジイソシアネート(IPDI、30.45mmol、6.77g)、ジブチルスズジラウレート(DBTDL、50mg)を溶かしたジメチルアセトアミド(DMAc)5mlをゆっくりと滴加し、2時間撹拌した。
PTMEGの投入量を16.5g(16.5mmol)と、HDSの投入量を3.13g(12.5mmol)と変更した以外は、すべての工程を実施例1と同様に行った。
PTMEGの投入量を18.5g(18.5mmol)と、HDSの投入量を2.63g(10.5mmol)と変更した以外は、すべての工程を実施例1と同様に行った。
PTMEGの投入量を20.5g(20.5mmol)と、HDSの投入量を2.13g(8.5mmol)と変更した以外は、すべての工程を実施例1と同様に行った。
PTMEGの投入量を22.5g(22.5mmol)と、HDSの投入量を1.63g(6.5mmol)と変更した以外は、すべての工程を実施例1と同様に行った。
PTMEGの投入量を24.5g(24.5mmol)と、HDSの投入量を1.13g(4.5mmol)と変更した以外は、すべての工程を実施例1と同様に行った。
実施例1でIPDI(30.45mmol、6.77g)の代わりに、IPDI(20.45mmol、4.55g)とヘキサメチレンジイソシアネート(HDI、10.00mmol、1.68g)の混合物を投入した以外は、すべての工程を実施例1と同様に行った。
実施例1でIPDI(30.45mmol、6.77g)の代わりに、IPDI(10.45mmol、2.32g)とHDI(20.00mmol、3.36g)の混合物を投入した以外は、すべての工程を実施例1と同様に行った。
実施例1でIPDI(30.45mmol、6.77g)の代わりに、IPDI(5.45mmol、1.21g)とHDI(25.00mmol、4.21g)の混合物を投入した以外は、すべての工程を実施例1と同様に行った。
実施例1でHDS(14.5mmol、3.63g)の代わりに、ビス(4‐アミノフェニル)ジスルフィド(ADS、14.5mmol、3.60g)を投入した以外は、すべての工程を実施例1と同様に行った。
実施例1でIPDI(30.45mmol、6.77g)の代わりに、HDI(30.45mmol、5.12g)を投入した以外は、すべての工程を実施例1と同様に行った。
実施例1でIPDI(30.45mmol、6.77g)の代わりに、ビス(4‐イソシアネートフェニル)メタン(MDI、30.45mmol、7.62g)を投入した以外は、すべての工程を実施例1と同様に行った。
実施例1でHDS(14.5mmol、3.63g)の代わりに、2‐ヒドロキシエチルジスルフィド(HEDS、14.5mmol、2.24g)を投入した以外は、すべての工程を実施例1と同様に行った。
実施例1〜9、および比較例1〜4から製造された重合体の物性は、下記のような方法で測定し、その結果を下記表2に記載した。
Claims (9)
- 下記化学式1で表される芳香族ジスルフィドジオール、脂環族ポリイソシアネートおよびポリオールを含む組成物から重合される、自己修復性ポリウレタン系重合体。
- 前記脂環族ポリイソシアネートは、イソホロンジイソシアネート、4,4´‐ジシクロヘキシルメタンジイソシアネート、シクロヘキシレンジイソシアネート、メチルシクロヘキシレンジイソシアネート、ビス(2‐イソシアナトエチル)‐4‐ジクロヘキセン‐1,2‐ジカルボキシレートおよび2,5‐ノルボルナンジイソシアネートおよび2,6‐ノルボルナンジイソシアネートから選択されるいずれか一つまたは二つ以上である、請求項1に記載の自己修復性ポリウレタン系重合体。
- 前記組成物は、下記関係式1を満たす、請求項1に記載の自己修復性ポリウレタン系重合体。
[関係式1]
0.1≦M[disulfide]/M[OH]
(前記関係式1中、M[disulfide]は、組成物中の芳香族ジスルフィドジオールの合計モル数であり、M[OH]は、組成物中の芳香族ジスルフィドジオールおよびポリオールの合計モル数である。) - 前記自己修復性ポリウレタン系重合体は、25℃の温度条件で50%以上の自己修復率を有する、請求項1に記載の自己修復性ポリウレタン系重合体。
- 前記自己修復性ポリウレタン系重合体は、下記関係式2の靭性回復率を満たす、請求項1に記載の自己修復性ポリウレタン系重合体。
[関係式2]
50≦T1/T0×100
(前記関係式2中、T0は、自己修復性ポリウレタン系重合体の切断前の靭性(MJ/m3)であり、T1は、自己修復性ポリウレタン系重合体を切断し、25℃の温度条件で2時間再接合した後の靭性(MJ/m3)である。) - 前記組成物は、脂肪族ポリイソシアネートおよび芳香族ポリイソシアネートから選択されるいずれか一つまたは二つ以上をさらに含む、請求項1に記載の自己修復性ポリウレタン系重合体。
- 前記組成物は、下記関係式3を満たす、請求項6に記載の自己修復性ポリウレタン系重合体。
[関係式3]
0.15≦M[cycloaliphatic]/M[NCO]≦1
(前記関係式1中、M[cycloaliphatic]は、組成物中の脂環族ポリイソシアネートの合計モル数であり、M[NCO]は、組成物中のポリイソシアネート系化合物の合計モル数である。) - 下記化学式1で表される芳香族ジスルフィドジオール、脂環族ポリイソシアネートおよびポリオールを含む組成物を重合するステップを含む、自己修復性ポリウレタン系重合体の製造方法。
- 請求項1から7のいずれか1項に記載の自己修復性ポリウレタン系重合体を含む、自己修復性ポリウレタン系コーティング膜。
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KR101830749B1 (ko) | 2017-07-12 | 2018-04-04 | 한국화학연구원 | 자가복원 폴리우레탄계 중합체 및 이의 제조방법 |
US11066574B2 (en) * | 2018-05-29 | 2021-07-20 | Nano And Advanced Materials Institute Limited | Self-healing coating compositions |
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KR102611792B1 (ko) * | 2021-06-23 | 2023-12-08 | 한국신발피혁연구원 | 자가 치유 코팅용 수분산체 조성물 |
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