Abstract
Oil/organic solvent leakage will pose a serious threat to the environment and ecology, and efficient oil/water separation has attracted much attention in recent years. Herein, we report a new conjugated microporous polymers based on tristyryl-s-triazine unit (CMP-TST) through the coupling reaction of 2,4,6 tribromostyryl-s-triazine (TBST) with 1,4 p-phenylenediacetylene monomers. Owning to the highly conjugated structure composed of C = C double bonds and C≡C triple bonds, CMP-TST exhibits super-hydrophobicity, rich porous structure as well as excellent chemical stability in hash conditions. Furthermore, CMP-TST can be coated on the skeleton of the polyurethane (PU) sponge, which endows the PU sponge with super-hydrophobicity, high elasticity, rich macroporous structure, and good mechanical stability. Ultimately, the coated PU sponge maintains its original superhydrophobicity even under extremely acidic/alkaline conditions (pH = 1–14). Importantly, the superhydrophobic CMP-TST@PU sponge can absorb low-density grease to saturation within 10 s, and its adsorption saturation capacity can be up to 72 times of its own weight. In addition, CMP-TST@PU can efficiently separate a series of different oil/water mixtures, including floating oil and bottom oil, with oil content greater than 99.8%. Besides, the superhydrophobic CMP-TST@PU sponge can continuously absorb and discharge oil and organic solvents on the water surface by means of vacuum, and the separation efficiency remains unchanged after repeated 10 times, indicating good cycle stability. It is worth mentioning that the sponge can also demulsify the surfactant-stabilized oil-in-water emulsion, and the purity of the recovered oil in the filtrate is about 99.8%. The fast adsorption capacity, excellent absorption capacity, outstanding reproducibility, and good stability make CMP-TST@PU a competitive candidate in dealing with large-scale oil pollution.
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10934-021-01180-3/MediaObjects/10934_2021_1180_Fig1_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10934-021-01180-3/MediaObjects/10934_2021_1180_Fig2_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10934-021-01180-3/MediaObjects/10934_2021_1180_Fig3_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10934-021-01180-3/MediaObjects/10934_2021_1180_Fig4_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10934-021-01180-3/MediaObjects/10934_2021_1180_Fig5_HTML.jpg)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10934-021-01180-3/MediaObjects/10934_2021_1180_Fig6_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10934-021-01180-3/MediaObjects/10934_2021_1180_Fig7_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10934-021-01180-3/MediaObjects/10934_2021_1180_Fig8_HTML.jpg)
Similar content being viewed by others
References
Z. Xiao, M. Zhang, W. Fan, Y. Qian, Z. Yang, B. Xu, Z. Kang, R. Wang, D. Sun, Chem. Eng. J. 326, 640–646 (2017)
J. Wan, L.-H. Xu, H. Pan, L.M. Wang, Y. Shen, J. Porous Mat. 28, 1501–1510 (2021)
K. Chen, W. Gou, X. Wang, C. Zeng, F. Ge, Z. Dong, C. Wang, ACS Sustain Chem Eng. 6, 16616–16628 (2018)
H. Cao, J. Fu, Y. Liu, S. Chen, Colloid Surface A 537, 294–302 (2018)
S. He, Y. Zhan, J. Hu, G. Zhang, S. Zhao, Q. Feng, W. Yang, Compos Part B-Eng 197, 108188 (2020)
J.T. Korhonen, M. Kettunen, R.H. Ras, ACS Appl. Mater. Inter. 3, 1813–1816 (2011)
X. Chen, L. Hong, Y. Xu, Z.W. Ong, A.C.S. Appl, Mater. Inter. 4, 1909–1918 (2012)
R. Du, Q. Zhao, P. Li, H. Ren, X. Gao, J. Zhang, A.C.S. Appl, Mater. Inter. 8, 1025–1032 (2016)
J. Gu, P. Xiao, P. Chen, L. Zhang, H. Wang, L. Dai, L. Song, Y. Huang, J. Zhang, T. Chen, A.C.S. Appl, Mater. Inter. 9, 5968–5973 (2017)
S. Huang, A.C.S. Appl, Mater. Inter. 6, 17144–17150 (2014)
X. Liu, L. Ge, W. Li, X. Wang, F. Li, A.C.S. Appl, Mater. Inter. 7, 791–800 (2015)
Y. Cao, N. Liu, W. Zhang, L. Feng, Y. Wei, A.C.S. Appl, Mater. Inter. 8, 3333–3339 (2016)
H. Sun, A. Li, X. Qin, Z. Zhu, W. Liang, J. An, P. La, W. Deng, Chemsuschem 6, 2377–2381 (2013)
A. Xie, J. Dai, C. Ma, J. Cui, Y. Chen, J. Lang, M. Gao, C. Li, Y. Yan, Appl. Surf. Sci. 462, 659–668 (2018)
C. Zhou, J. Cheng, K. Hou, A. Zhao, P. Pi, X. Wen, S. Xu, Chem. Eng. J. 301, 249–256 (2016)
E.C. Cho, W. Chang, C.W. Jian, H.C. Chen, K.S. Chuang, J.H. Zheng, Y.S. Hsiao, K.C. Lee, J.H. Huang, Chem. Eng. J. 314, 347–357 (2017)
S. Xie, L. Guo, M. Zhang, R. Hu, J. Porous Mat. 28, 1115–1127 (2021)
J. Song, S. Li, C. Zhao, Y. Lu, D. Zhao, J. Sun, T. Roy, C.J. Carmalt, X. Deng, I.P. Parkin, Nanoscale 10, 1920–1929 (2018)
X. Li, W. Zhang, R. Qu, Y. Liu, Y. Wei, L. Feng, J. Mater. Chem. A. 7, 10047–10057 (2019)
M. Wang, M. Peng, J. Zhu, Y.D. Li, J.B. Zeng, Carbohyd. Polym. 244, 116449 (2020)
J. Zhang, S. Seeger, Adv. Funct. Mater. 21, 4699–4704 (2011)
W. Zhang, X. Zhai, T. Xiang, J. Mater. Sci. 52, 73–85 (2016)
Y. Chen, N. Li, S. Mo, Q. Xu, Ind. Eng. Chem. Res. 52, 16190–16196 (2013)
Y. Tang, H. Huang, X. Guo, C. Zhong 59, 13228–13238 (2020)
C. Chen, D. Weng, A. Mahmood, S. Chen, J. Wang, A.C.S. Appl, Mater. Inter. 11, 11006–11027 (2019)
M. Ge, C. Cao, J. Huang, X. Zhang, Y. Tang, X. Zhou, K. Zhang, Z. Chen, Y. Lai, Nanoscale 3, 235–260 (2018)
J. Gu, H. Fan, C. Li, J. Caro, H. Meng, Angew. Chem. Int. Ed. 131, 5351–5355 (2019)
Y. Sun, Q. Sun, H. Huang, B. Aguila, Z. Niu, J.A. Perman, S. Ma, J. Mater. Chem. A. 5, 18770–18776 (2017)
Y. Jiang, C. Liu, Y. Li, A. Huang, J. Membr. Sci. 587, 117177 (2019)
M. Zhang, X. Xin, Z. Xiao, R. Wang, L. Zhang, D. Sun, J. Mater. Chem. A. 5, 1168–1175 (2017)
M.L. Gao, S.Y. Zhao, Z.Y. Chen, L. Liu, Z.B. Han, Inorg. Chem. 58, 2261–2264 (2019)
L. Xu, Y. Zang, J. Xiao, Y. Wu, Y. Pan, T. Wu, Y. Tang, J. Cui, H. Jia, F. Miao, Sep. Purif. Technol. 261, 118291 (2021)
Y. Lei, Z. Tian, H. Sun, F. Liu, Z. Zhu, W. Liang, A. Li, A.C.S. Appl, Mater. Inter. 13, 5823–5833 (2021)
Z. Chen, M. Chen, Y. Yu, L. Wu, Chem. Commun. 53, 1989–1992 (2017)
R. Morales, M.J. Martinez, A.M.R. Pilosof, Food Hydrocolloid 87, 805–813 (2019)
A. Raza, B. Ding, G. Zainab, M. El-Newehy, S.S. Al-Deyab, J. Yu, J. Mater. Chem. A. 2, 10137–10145 (2014)
X. Liu, Y. Xu, Z. Guo, A. Nagai, D. Jiang, Chem. Commun. 49, 3233–3235 (2013)
S. Jin, M. Supur, M. Addicoat, K. Furukawa, L. Chen, T. Nakamura, S. Fukuzumi, S. Irle, D. Jiang, J. Am. Chem. Soc. 137, 7817–7827 (2015)
W. Fan, X. Liu, Z. Zhang, Q. Zhang, W. Ma, D. Tan, A. Li, Micropor Mesopor Mat. 196, 335–340 (2014)
K. Wang, H. Huang, D. Liu, C. Wang, J. Li, C. Zhong, Environ. Sci. Technol. 50, 4869–4876 (2016)
Y. Tang, H. Huang, W. Xue, Y. Chang, Y. Li, X. Guo, C. Zhong, Chem. Eng. J. 384, 123382 (2020)
C.-M. Yu, X.-H. Zhuang, S.-W Zeng, Q.-X. Dong, Z.-X. Jing, P.-Z. Hong, Y. Li, RSC Adv. 9, 17543–17550 (2019)
H. Wang, E. Wang, Z. Liu, D. Gao, R. Yuan, L. Sun, Y. Zhu, J. Mater. Chem. A. 3, 266–273 (2015)
C.-F. Wang, S.-J. Lin, A.C.S. Appl, Mater. Inter. 5, 8861–8864 (2013)
L. Wu, L. Li, B. Li, J. Zhang, A. Wang, A.C.S. Appl, Mater. Inter. 7, 4936–4946 (2015)
J. Li, C. Xu, Y. Zhang, R. Wang, F. Zha, H. She, J. Mater. Chem. A. 4, 15546–15553 (2016)
S.-J. Choi, T.-H. Kwon, H. Im, D.I. Moon, D.J. Baek, M.-L. Seol, J.P. Duarte, Y.-K. Choi, A.C.S. Appl, Mater. Inter. 3, 4552–4556 (2011)
J. Zhang, Z. Meng, J. Liu, C. Schlaich, Z. Yu, X. Deng, J. Mater. Chem. A. 5, 16369–16375 (2017)
L. Zhang, L. Xu, Y. Sun, N. Yang, Ind. Eng. Chem. Res. 55, 11260–11268 (2016)
M. Ramiro, E. SerraEduardo, V.-B. MiróAlicia, Micropor. Mesopor. Mater. 127, 182–189 (2010)
M.-H. Aziz, A.-A. Jalil, T.-J. Siang, I. Hussain, A.-A. Rahman, H. Hamdan, Fuel 305, 121432 (2021)
Y. Ding, J. Wu, J. Wang, H. Lin, J. Wang, G. Liu, X. Pei, F. Liu, C.Y. Tang, Appl. Surf. Sci. 485, 179–187 (2019)
Acknowledgements
The authors are grateful for support from the National Natural Science Foundation of China (No. 22038010, 21878229, and 21978212), and the Science and Technology Plans of Tianjin (20ZYJDJC00110 and19PTSYJC00020). We also would like to thank the Analytical & Testing Center of Tiangong University for providing some analytical testing.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare no conflicts of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Supplementary file1 (MP4 2328 kb)
Supplementary file2 (MP4 625 kb)
Supplementary file3 (MP4 6244 kb)
Rights and permissions
About this article
Cite this article
Zheng, M., Huang, H., Jiang, Z. et al. Superhydrophobic conjugated porous organic polymer coated polyurethane sponge for efficient oil/water separation. J Porous Mater 29, 433–444 (2022). https://doi.org/10.1007/s10934-021-01180-3
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10934-021-01180-3