Synthesis and characterization of caprolactone based polyurethane with degradable and antifouling performance

doi:10.1016/j.cjche.2020.11.007

Chinese Journal of Chemical Engineering ›› 2021, Vol. 34 ›› Issue (6): 299-306.DOI: 10.1016/j.cjche.2020.11.007

Synthesis and characterization of caprolactone based polyurethane with degradable and antifouling performance

Abid Ali¹, Lina Song¹, Jiankun Hu², Jingxian Jiang¹, Qingqing Rao¹, Muhammad Shoaib¹, Shah Fahad¹, Yongjie Cai¹, Xiaoli Zhan^1,2, Fengqiu Chen¹, Qinghua Zhang^1,2

1 College of Chemical and Biological Engineering, Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering, Manufacture Technology, Zhejiang University, Hangzhou 310027, China;
2 Ningbo Research Institute, Zhejiang University, Ningbo 315100, China

Received:2020-07-22 Revised:2020-11-14 Online:2021-08-30 Published:2021-06-28
Contact: Xiaoli Zhan, Qinghua Zhang
Supported by:
This work was supported by the National Natural Science Foundation of China (21776249, 21878267, and 21576236).

Synthesis and characterization of caprolactone based polyurethane with degradable and antifouling performance

Abid Ali¹, Lina Song¹, Jiankun Hu², Jingxian Jiang¹, Qingqing Rao¹, Muhammad Shoaib¹, Shah Fahad¹, Yongjie Cai¹, Xiaoli Zhan^1,2, Fengqiu Chen¹, Qinghua Zhang^1,2

1 College of Chemical and Biological Engineering, Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering, Manufacture Technology, Zhejiang University, Hangzhou 310027, China;
2 Ningbo Research Institute, Zhejiang University, Ningbo 315100, China

通讯作者: Xiaoli Zhan, Qinghua Zhang
基金资助:
This work was supported by the National Natural Science Foundation of China (21776249, 21878267, and 21576236).

Abstract

Abstract: In this work, a degradable polyurethane composed of caprolactone (CL) and L-Lactide (LLA) as soft segments, and 4,4’-methylenebis(cyclohexyl isocyanate) (H₁₂MDI) and polytetramethylene ether glycol (PTMEG) as hard segments, was prepared. Hydrolytic degradation experiment revealed that the degradable polyurethane (PU) could be degraded in artificial seawater. It also showed that caprolactone-copolyurethane (CL-PU) copolymer with higher crystallinity degraded much slower in artificial seawater. However, the introduction of LLA resulted in an increase in the hydrophilicity and reduction in the crystallinity of degradable PU, as demonstrated by the contact angle analysis. The result of the scanning electron microscope showed that the surface of degradable PU renewed under static condition. Moreover, degradable PU was able to be used as a carrier, and it controlled the release rate of 4, 5-dichloro-2- octyl-isothiazolone (DCOIT). The anti-diatom (Navicula incerta) test demonstrated that the (caprolactone-co-L-lactide)-co-polyurethane 4 (CL/LAx-PU4) with DCOIT contents prevented the adhesion of diatom Navicula incerta (88.37% reduction) due to their self-polishing and the release of antifoulants. Therefore, the degradable PU consisted of CL, LLA, and DCOIT could be a durable resin with good antifouling activity for the application in the marine anti-biofouling field.

Key words: Antifoulant, 4,5-dicholoro-2-octyl-isothiazolone, Degradable polyurethane, L-Lactide, Caprolactone

摘要： In this work, a degradable polyurethane composed of caprolactone (CL) and L-Lactide (LLA) as soft segments, and 4,4’-methylenebis(cyclohexyl isocyanate) (H₁₂MDI) and polytetramethylene ether glycol (PTMEG) as hard segments, was prepared. Hydrolytic degradation experiment revealed that the degradable polyurethane (PU) could be degraded in artificial seawater. It also showed that caprolactone-copolyurethane (CL-PU) copolymer with higher crystallinity degraded much slower in artificial seawater. However, the introduction of LLA resulted in an increase in the hydrophilicity and reduction in the crystallinity of degradable PU, as demonstrated by the contact angle analysis. The result of the scanning electron microscope showed that the surface of degradable PU renewed under static condition. Moreover, degradable PU was able to be used as a carrier, and it controlled the release rate of 4, 5-dichloro-2- octyl-isothiazolone (DCOIT). The anti-diatom (Navicula incerta) test demonstrated that the (caprolactone-co-L-lactide)-co-polyurethane 4 (CL/LAx-PU4) with DCOIT contents prevented the adhesion of diatom Navicula incerta (88.37% reduction) due to their self-polishing and the release of antifoulants. Therefore, the degradable PU consisted of CL, LLA, and DCOIT could be a durable resin with good antifouling activity for the application in the marine anti-biofouling field.

关键词: Antifoulant, 4,5-dicholoro-2-octyl-isothiazolone, Degradable polyurethane, L-Lactide, Caprolactone

Abid Ali, Lina Song, Jiankun Hu, Jingxian Jiang, Qingqing Rao, Muhammad Shoaib, Shah Fahad, Yongjie Cai, Xiaoli Zhan, Fengqiu Chen, Qinghua Zhang. Synthesis and characterization of caprolactone based polyurethane with degradable and antifouling performance[J]. Chinese Journal of Chemical Engineering, 2021, 34(6): 299-306.

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Synthesis and characterization of caprolactone based polyurethane with degradable and antifouling performance

Synthesis and characterization of caprolactone based polyurethane with degradable and antifouling performance

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