Abstract
Generally, dyeing and finishing of Bombyx mori silk fibers were proceeded at high temperature, which has the disadvantages of overmuch energy-consumptions. In the present work, bio-inspired in situ coloring and functionalization of silk fabric were carried out via laccase-catalyzed graft polymerization of arylamines, including aniline (ANI) and p-phenylenediamine (PPD). p-Hydroxyphenylacetamide (PHAD) as the model compound of tyrosine residues in silk fibroin (SF) was used to explore the mechanism of graft polymerization by means of MALDI-TOF MS. The actions of the dopants of sodium dodecyl benzene sulfonate (SDBS) and sodium p-aminobenzenesulfonate (ABSA) on the enzymatic treatment were also concerned. The results indicated that laccase might initiate the self-polymerizations of ANI and PPD, respectively, and formed the copolymers of arylamine and PHAD subsequently. High color depth and color fastness were obtained after incubation silk fabric with laccase and arylamines, companying with a noticeable pH-responsiveness. The laccase-mediated treatment endowed silk fabric with antibacterial and antioxidant abilities, meanwhile, the addition of dopants of SDBS and ABSA promoted the enzymatic finishing. Enzymatic graft polymerization of arylamine onto silk fibroin provides a novel approach for dyeing and functionalization of silk fabrics under mild treating conditions.
Similar content being viewed by others
References
D. H. Kim, J. Viventi, J. J. Amsden, J. Xiao, L. Vigeland, Y.-S. Kim, J. A. Blanco, B. Panilaitis, E. S. Frechette, and D. Contreras, Nat. Mater., 9, 511 (2010).
Y. Wang, D. D. Rudym, A. Walsh, L. Abrahamsen, H. J. Kim, H. S. Kim, C. Kirker-Head, and D. L. Kaplan, Biomaterials, 29, 3415 (2008).
M. Wang, H. J. Jin, D. L. Kaplan, and G. C. Rutledge, Macromolecules, 37, 6856 (2004).
C. Jiang, X. Wang, R. Gunawidjaja, Y. H. Lin, M. K. Gupta, D. L. Kaplan, R. R. Naik, and V. V. Tsukruk, Adv. Funct. Mater., 17, 2229 (2007).
M. D. Teli in “Advances in Silk Science and Technology” (A. Basu Ed.), p.55, Woodhead Publishing, 2015.
N. M. Parekh and K. C. Maheria, Res. Chem. Intermed., 40, 1003 (2014).
J. P. Guan and G. Q. Chen, Fire Mater., 30, 415 (2006).
G. H. R. Silva, L. A. Daniel, H. Bruning, and W. H. Rulkens, Bioresour. Technol., 101, 6981 (2010).
S. Kobayashi, H. Uyama, and S. Kimura, Chem. Rev., 101, 3793 (2001).
J. Polak, A. Jarosz-Wilkolazka, A. Szuster-Ciesielska, K. Wlizlo, M. Kopycinska, J. Sojka-Ledakowicz, and J. Lichawska-Olczyk, J. Cleaner Prod., 112, 4265 (2016).
H. Claus, Arch. Microbiol., 179, 145 (2003).
G. Alexandre and I. B. Zhulin, Trends Biotechnol., 18, 41 (2000).
A. Abou-Okeil, A. El-Shafie, and M. M. El Zawahry, Ultrason. Sonochem., 17, 383 (2010).
T. Senthivelan, J. Kanagaraj, and R. Panda, Biotechnol. Bioprocess Eng., 21, 19 (2016).
J. Su, J. Fu, Q. Wang, C. Silva, and A. Cavaco-Paulo, Crit. Rev. Biotechnol., 38, 294 (2018).
S. Kim, H. Lee, J. Kim, F. Oliveira, P. Souto, H. Kim, and J. Nakamatsu, J. Appl. Polym. Sci., 135, 45801 (2018).
J. Su, J. Noro, J. Fu, Q. Wang, C. Silva, and A. J. P. B. Cavaco-Paulo, Process Biochem., 77, 77 (2019).
T. Zhang, R. B. Bai, Q. Wang, X. R. Fan, P. Wang, J. G. Yuan, and Y. Y. Yu, Color Technol., 133, 65 (2017).
W. Jia, Q. Wang, X. Fan, A. Dong, Y. Yu, and P. Wang, RSC Adv., 7, 12977 (2017).
Q. Zhou, L. Cui, L. Ren, P. Wang, C. Deng, Q. Wang, and X. Fan, Int. J. Biol. Macromol., 113, 1062 (2018).
W. Jia, Q. Wang, X. Fan, A. Dong, Y. Yu, and P. Wang, Fiber. Polym., 19, 868 (2018).
P. Wang, C. Deng, J. Yuan, Y. Yu, L. Cui, M. Su, Q. Wang, and X. Fan, Biotechnol. Appl. Biochem., 63, 163 (2016).
B. Zhou, P. Wang, L. Cui, Y. Yu, C. Deng, Q. Wang, and X. Fan, Appl. Biochem. Biotechnol., 182, 1548 (2017).
Q. Zhou, L. Cui, L. Ren, P. Wang, C. Deng, Q. Wang, and X. Fan, Int. J. Biol. Macromol., 113, 1062 (2018).
M. He, H. Hu, P. Wang, H. Fu, J. Yuan, Q. Wang, and X. Fan, Int. J. Biol. Macromol., 117, 323 (2018).
B. Zhou, M. He, P. Wang, H. Fu, Y. Yu, Q. Wang, and X. Fan, Mater. Sci. Eng. CMater. Biol. Appt., 81, 291 (2017).
E. Bendary, R. R. Francis, H. M. G. Ali, M. I. Sarwat, and S. El Hady, Ann. Agri. Sci., 58, 173 (2013).
N. Shi, X. Guo, H. Jing, J. Gong, C. Sun, and Y. Ke, J. Mater. Sci. Technol., 22, 289 (2009).
J. Y. Yao, Y. F. Chen, W. D. Li, X. Chen, and X. D. Fan, RSCAdv., 9, 5610 (2019).
S. Y. Chin, T. K. Abdullah, and M. Mariatti, J. Mater. Sci-Mater. EL., 28, 18418 (2017).
I. Amer, T. Mokrani, L. Jewell, D. A. Young, and H. C. M. Vosloo, Tetrahedron Lett., 57, 426 (2016).
G. P. Song and D. X. Xia, Acta Phys-Chim Sin., 30, 583 (2014).
D. Zhang and Y. Wang, Mater. Sci. Eng. B, 134, 9 (2006).
G. Li, S. Pang, H. Peng, Z. Wang, Z. Cui, and Z. Zhang, J. Polym. Sci., Part A: Polym. Chem., 43, 4012 (2005).
A. V. Nand, S. Ray, A. J. Easteal, G. I. N. Waterhouse, M. Gizdavic-Nikolaidis, R. P. Cooney, J. Travas-Sejdic, and P. A. Kilmartin, Synth. Met., 161, 1232 (2011).
M. Gizdavic-Nikolaidis, J. Travas-Sejdic, P. A. Kilmartin, G. A. Bowmaker, and R. P. Cooney, Curr. Appl. Phys., 4, 343 (2004).
E. Bendary, R. R. Francis, H. M. G. Ali, M. I. Sarwat, and S. El Hady, Ann. Agri. Sci., 58, 173 (2013).
Q. Zhou, L. Cui, L. Ren, P. Wang, C. Deng, Q. Wang, and X. Fan, Int. J. Biol. Macromol., 113, 1062 (2018).
C. F. Hsu, H. Peng, C. Basle, J. Travas-Sejdic, and P. A. Kilmartin, Polym. Int., 60, 69 (2011).
Acknowledgments
This work was financially supported by Six Talent Peaks Projects in Jiangsu Province (XCL-133), the National Natural Science Foundation of China (31771039), the Fundamental Research Funds for the Central Universities (JUSRP51717A) and the 111 Project (B17021).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Nong, Y., Zhou, Z., Yuan, J. et al. Bio-Inspired Coloring and Functionalization of Silk Fabric via Laccase-Catalyzed Graft Polymerization of Arylamines. Fibers Polym 21, 1927–1937 (2020). https://doi.org/10.1007/s12221-020-1044-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12221-020-1044-9