Synthesis, Dye Encapsulation, and Highly Efficient Colouring Application of Amphiphilic Hyperbranched Polymers
Zhulin Weng A B , Yaochen Zheng A C , Aijin Tang A and Chao Gao A DA MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University,Hangzhou 310027, China.
B Department of Physics, Hubei University for Nationalities, Enshi, Hubei 445000, China.
C Department of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China.
D Corresponding author. Email: chaogao@zju.edu.cn
Professor Chao Gao received his Ph.D. in 2001 from Shanghai Jiao Tong University, and was promoted to full professor in 2008 at the Department of Polymer Science and Engineering, Zhejiang University, after post-doctoral research at the University of Sussex and Bayreuth University. His research interests include hyperbranched polymers and graphene chemistry. He has co-edited a book on hyperbranched polymers and published 100 peer-reviewed papers. The graphene fibre knot from his research was selected by Nature as one of the “Images of the Year” in 2011. He now serves as the regional editor of Colloid and Polymer Science. |
Australian Journal of Chemistry 67(1) 103-111 https://doi.org/10.1071/CH13353
Submitted: 5 July 2013 Accepted: 12 September 2013 Published: 23 October 2013
Abstract
A novel kind of amphiphilic hyperbranched polymer (AHP), poly(2-(dimethylamino)ethyl methacrylate)-co-polystyrene (HPTAM-co-PS), was synthesized via the combination of reversible addition–fragmentation chain-transfer polymerization and self-condensing vinyl polymerization (RAFT-SCVP). HPTAM-co-PS was functionalized via the highly efficient Menschutkin click reaction, resulting in hyperbranched poly(propargyl quaternary ammonium methacrylate)-co-polystyrene (HPPrAM-co-PS) with a hydrophilic quaternary ammonium salt core and hydrophobic PS shell. The average numbers of dye molecules trapped by each molecule of HPPrAM-co-PS (24.2 kDa) were 24.1 for methyl orange (MO), 22.0 for fluorescein sodium (FS), 24.2 for rose bengal (RB), and 238.4 for Congo red (CR). The polymer–dye complexes show excellent colouring effects for both PS and poly(styrene-b-butadiene-b-styrene) (SBS) membranes; the colour of the membrane containing AHP is very stable and uniform. Our work opens an avenue for the design of efficient dye-colouring additives and for the application of hyperbranched polymers in the field of polymer colouring.
References
[1] Z. Hao, A. Iqbal, Chem. Soc. Rev. 1997, 26, 203.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXlt1Wmurg%3D&md5=426d64281e23eb1cc2b3848da3a80396CAS |
[2] C. Gao, D. Yan, Prog. Polym. Sci. 2004, 29, 183.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhs1CrsL8%3D&md5=23bec761c2bdd4b306d867dfd9092273CAS |
[3] P. J. Flory, J. Am. Chem. Soc. 1952, 74, 2718.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG38Xls1ertQ%3D%3D&md5=ec38446f56c565ee551dbb1443e22b0eCAS |
[4] Y. H. Kim, O. W. Webster, J. Am. Chem. Soc. 1990, 112, 4592.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXitFOltro%3D&md5=ce3c5884134961d6bf5ea3d2b3a164fdCAS |
[5] Y. H. Kim, J. Polym. Sci. A Polym. Chem. 1998, 36, 1685.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXksVOhtLc%3D&md5=91372674c1f3480e09037ea778e130c8CAS |
[6] B. Voit, J. Polym. Sci. A Polym. Chem. 2000, 38, 2505.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXkt1aqsbY%3D&md5=e9122526a982c67ffd1ca9a67a7c421dCAS |
[7] M. Jikei, M. Kakimoto, Prog. Polym. Sci. 2001, 26, 1233.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXptFCisro%3D&md5=d080dbbafa7c97256231addda0f44c92CAS |
[8] C. Gao, in Hyperbranched Polymers and Functional Nanoscience (Ed. M. Adeli) 2008, Ch. 2, pp. 33–71 (Transworld Research Network: Kerala).
[9] X. Hu, L. Zhou, C. Gao, Colloid Polym. Sci. 2011, 289, 1299.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXnvVKmt7o%3D&md5=438fbc8a0435c111b8ffcc0ec9ade1d9CAS |
[10] M. Krämer, J. F. Stumbé, H. Turk, S. Krause, A. Komp, L. Delineau, S. Prokhorova, H. Kautz, R. Haag, Angew. Chem. Int. Ed. 2002, 41, 4252.
| Crossref | GoogleScholarGoogle Scholar |
[11] C. H. Liu, C. Gao, D. Y. Yan, Chem. Res. Chin. Univ. 2005, 21, 345.
| 1:CAS:528:DC%2BD2MXltFOqsb0%3D&md5=7021f7b915b9045ca01dd86487282a7eCAS |
[12] C. Liu, C. Gao, D. Yan, Macromolecules 2006, 39, 8102.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtVKmsLfO&md5=f565ea59aab954a215e52c280ad98978CAS |
[13] C. Liu, C. Gao, D. Yan, Angew. Chem. Int. Ed. 2007, 46, 4128.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmtlOkt7o%3D&md5=7903044e3540872bd50426da3d8125d4CAS |
[14] Y. L. Su, X. R. Li, Y. J. Tong, Y. S. Li, Chin. J. Polym. Sci. 2003, 22, 1.
| 1:CAS:528:DC%2BD2cXotFOrsA%3D%3D&md5=b8178d5ffd7ffe0fc60c4684e403121cCAS |
[15] L. Tang, Y. Fang, X. Tang, J. Polym. Sci. A. Polym. Chem. 2005, 43, 2921.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXls1Grsrw%3D&md5=e1604a281e66a38c091d885020db740dCAS |
[16] Y. Lin, X. Liu, Z. Dong, B. Li, X. Chen, Y. Li, Biomacromolecules 2008, 9, 2629.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXpslegt78%3D&md5=e9ff3c5b481180cd32d56de9d386b197CAS | 18698818PubMed |
[17] Y. Fang, L. M. Tang, T. Qiu, D. C. Qi, Acta Polym. Sin. 2004, 2, 309.
[18] C. H. Liu, C. Gao, H. Zeng, D. Y. Yan, Chem. J. Chinese U. 2005, 26, 1941.
| 1:CAS:528:DC%2BD2MXhtFOjt7jM&md5=6b463acae94ef4ce05556ee9ea30f14dCAS |
[19] J. Han, C. Gao, Curr. Org. Chem. 2011, 15, 2.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXkslaitr4%3D&md5=6bf34f0573fa16594faf5ef8f520c8efCAS |
[20] N. Kihara, K. Hinoue, T. Takata, Macromolecules 2005, 38, 223.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhvA%3D%3D&md5=fe48ef0a6d600fbb4209d7190be9d437CAS |
[21] D. Wan, H. Pu, X. Cai, Macromolecules 2008, 41, 7787.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1ertbjJ&md5=b61ba7babfef77bbbaf5c90137fba8fdCAS |
[22] Y. Chen, Z. Shen, L. Pastor-Pérez, H. Frey, S.-E. Stiriba, Macromolecules 2005, 38, 227.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtFCrurzL&md5=491b59dcc7b81d5141dc3358a18138a2CAS |
[23] S. M. Burkinshaw, P. E. Froehling, M. Mignanelli, Dyes Pigments 2002, 53, 229.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xjsl2gsbs%3D&md5=67cc104eefb732a3297236523c112359CAS |
[24] F. Zhang, Y. Chen, H. Lin, Y. Lu, Color. Technol. 2007, 123, 351.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVersbbN&md5=ed01c5dfc405ab285b599e2690770d7aCAS |
[25] F. Zhang, Y. Chen, H. Lin, H. Wang, B. Zhao, Carbohydr. Polym. 2008, 74, 250.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXosFSlsLY%3D&md5=3734d268d00e796b28fff952ad626ca2CAS |
[26] D. Schmaljohann, P. Pötschke, R. Hässler, B. I. Voit, P. E. Froehling, B. Mostert, J. A. Loontjens, Macromolecules 1999, 32, 6333.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXlt1ant70%3D&md5=d9bbdc2b748d5d1513c72323dd5c5aeaCAS |
[27] A. Tang, J. Han, Z. Weng, C. Gao, Acta Polym. Sin. 2013, 1, 70.
| Crossref | GoogleScholarGoogle Scholar |
[28] J. Han, S. Li, A. Tang, C. Gao, Macromolecules 2012, 45, 4966.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XoslanurY%3D&md5=bf0332667a418481137e8405e838d34dCAS |
[29] S. Li, J. Han, C. Gao, Polym. Chem. 2013, 4, 1774.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXivVKqtr4%3D&md5=ea1ea4860d306a7652f39642fffcd0bcCAS |
[30] H. Mori, M. Tsukamoto, Polymer 2011, 52, 635.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtlKrurg%3D&md5=4897d8430250f0541fcdc24e531f3c4bCAS |
[31] C. J. Hawker, J. M. J. Frechet, R. B. Grubbs, J. Dao, J. Am. Chem. Soc. 1995, 117, 10763.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXosF2jsbc%3D&md5=eda726c91588df7cebbc3fc756854be7CAS |
[32] J. M. J. Fréchet, M. Henmi, I. Gitsov, S. Aoshima, M. R. Leduc, R. B. Grubbs, Science 1995, 269, 1080.
| Crossref | GoogleScholarGoogle Scholar |
[33] V. Chechik, M. Zhao, R. M. Crooks, J. Am. Chem. Soc. 1999, 121, 4910.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXivVaksbk%3D&md5=0ad643bd536a05ae5b3e482a54d6c6bfCAS |
[34] Y. Kitajyo, Y. Nawa, M. Tamaki, H. Tani, K. Takahashi, H. Kaga, T. Satoh, T. Kakuchi, Polymer 2007, 48, 4683.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXotVanurY%3D&md5=2254c6c65bb524cde878bab197cb749eCAS |
[35] H. He, Y. Zhang, C. Gao, J. Wu, Chem. Commun. 2009, 1655,
| Crossref | GoogleScholarGoogle Scholar |
[36] B. Iskin, G. Yilmaz, Y. Yagci, J. Polym. Sci. A Polym. Chem. 2011, 49, 2417.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXkvFGgt78%3D&md5=3ba643b11a1b4e4f0e079a93c8d5f018CAS |
