A couple of novel sulfobetaine copolymer is developed via Michael-type addition reaction. The comonomers, diamines and maleimide react via Michael reaction through UV irradiation using AIBN as photoinitiator producing polyamine chain. Further, sulfobetaine copolymers were obtained on treatment of the polyamine with sulfopropylating agent, 1,3-propane sultone. These novel sulfobetaine polymers were grafted on silica surface to produce responsive biocompatible surface. This easy straightforward, catalyst free facile protocol for synthesis of polymer grafted surface is useful for developing biomedical devices. Additionally, both the copolymers show fluorescence characteristics.
KeywordsCopolymerSulfobetaineZwitterionicGrafted CopolymerPhotopolymerizationMaleimideMichael-Type ReactionSurface Initiated Polymerization (SIP)Density Functional Theory (DFT)Fluorescence
M. Ozdemir, C. U. Yurteri and H.Sadikoglu, “Physical Polymer Surface Modification Methods and Applications in Food Packaging Polymers,” Critical Reviews in Food Science and Nutrition, Vol. 39, No. 5, 1999, pp. 457-477. doi:10.1080/10408699991279240
Z. Jia, S. Du and G. Tian, “Surface Modification of Acrylic Fiber by Grafting of Casein,” Journal of Macro- molecular Science, Part A: Pure and Applied Chemistry, Vol. 44, No. 3, 2007, pp. 299-304. doi:10.1080/10601320601077351
M. Suzuki, A. Kishida, H. Iwata and Y. Ikada, “Graft Copolymerization of Acrylamide onto a Polyethylene Surface Pretreated with Glow Discharge,” Macromole- cules, Vol. 19, No. 7, 1986, pp.1804-1808. doi:10.1021/ma00161a005
M. Onishi, K. Shimura, Y. Seita, S. Yamashita, A. Taka- hashi and T. Masuoka, “Preparation and Properties of Plasma-Initiated Graft Copolymerized Membranes for Blood Plasma Separation,” International Journal of Ra- diation Applications and Instrumentation. Part C. Radia- tion Physics and Chemistry, Vol. 39, No. 6, 1992, pp. 569-576. doi:10.1016/1359-0197(92)90114-U
D. S. Wavhal and E. R. Fisher, “Hydrophilic Modifica- tion of Polyethersulfone Membranes by Low Temperature Plasma-Induced Graft Polymerization,” Journal of Mem- brane Science, Vol. 209, No. 1, 2002, pp. 255-259. doi:10.1016/S0376-7388(02)00352-6
Y. Q. Song, J. Sheng, M. Wei and X. B. Yuan, “Surface Modification of Polysulfone Membranes by Low-Tem- perature Plasma-Graft Poly(Ethylene Glycol) onto Poly- sulfone Membranes,” Journal of Applied Polymer Science, Vol. 78, No. 5, 2000, pp. 979-985. doi:10.1002/1097-4628(20001031)78:5 3.0.CO;2-U
J. Lei, X. Liao and D. Lin, “Studies on Surface Graft Copolymerization of Acrylic Acid onto LDPE Film through Corona Discharge,” Chemical Journal on Internet, Vol. 2, 2000, Article ID: 021006pc.
J. Lei, Q. Li, G. He and X. Lin, “Surface Graft Copoly- merization of Acrylic Amide onto BOPP Film through Corona Discharge,” Acta Chimica Sinica, Vol. 58, No. 5, 2000, pp. 598-600.
J. Lei, M. Shi and J. Zhang, “Surface Graft Copolymeri- zation of Hydrogen Silicon Fluid onto Fabric through Corona Discharge and Water Repellency of Grafted Fab- ric,” European Polymer Journal, Vol. 36, No. 6, 2000, pp. 1277-1281. doi:10.1016/S0014-3057(99)00169-X
S. Mok, D. J. Worsfold, A. Founda and T. Matsuura, “Surface Modification of Poly(Ether Sulfone) Hollow- Fiber Membranes by γ-Ray Irradiation,” Journal of Ap- plied Polymer Science, Vol. 51, No. 1, 1994, pp. 193-199. doi:10.1002/app.1994.070510120
A. F. Filho and A. S. Gomes, “Copolymerization of Sty- rene onto Polyethersulfone Films Induced by Gamma Ray Irradiation,” Polymer Bulletin, Vol. 57, No. 4, 2006, pp. 415-421. doi:10.1007/s00289-006-0574-7
E. Bucio, E. Arenas and G. Burillo, “Radiation Grafting of N-Isopropylacrylamide onto Polypropylene Films by Preirradiation Method,” Molecular Crystals and Liquid Crystals, Vol. 447, No. 1, 2006, pp. 521-531. doi:10.1080/15421400500387593
J. Deng, L. Wang, L. Liu and W. Yang, “Developments and New Applications of UV-Induced Surface Graft Po- lymerizations,” Progress in Polymer Science, Vol. 34, No. 2, 2009, pp. 156-194. doi:10.1016/j.progpolymsci.2008.06.002
G. Oster and O. Shibata, “Graft Copolymer of Polyacryla- mide and Natural Rubber Produced by Means of Ultra- violet Light,” Journal of Polymer Science, Vol. 26, No. 113, 1957, pp. 233-234. doi:10.1002/pol.1957.1202611311
B. Kasemo and J. Gold, “Graft Copolymer of Polyacryla- mide and Natural Rubber Produced by Means of Ultra- violet Light,” Advances in Dental Research, Vol. 13, No. 1, 1999, pp. 8-20. doi:10.1177/08959374990130011901
F. H. Jones, “Teeth and Bones: Applications of Surface Science to Dental Materials and Related Biomaterials,” Surface Science Reports, Vol. 42, No. 3-6, 2001, pp. 75-205. doi:10.1016/S0167-5729(00)00011-X
D. Klee and H. Hocker, “Advances in Polymer Science: Biomedical Application/Polymer Blends,” Biomedical Applications Polymer Blends, Vol. 149, 1999, pp. 1-55. doi:10.1007/3-540-48838-3_1
B. D. Mather, K. Viswanathan, K. M. Miller and T. E. Long, “Michael Addition Reactions in Macromolecular Design for Emerging Technologies,” Progress in Polymer Science, Vol. 31, No. 5, 2006, pp. 487-531. doi:10.1016/j.progpolymsci.2006.03.001
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, et al., “Gaussian 03, Revi- sion D.01,” Gaussian, Inc., Wallingford CT, 2004.
W. Roberts and W. L. D. Liams, “Sultone Chemistry,” Tetrahedron, Vol. 43, No. 6, 1987, pp. 1027-1062. doi:10.1016/S0040-4020(01)90041-9
K. D. Schmitt, “Surfactant-Mediated Phase Transfer as an Alternative to Propanesultone Alkylation. Formation of a New Class of Zwitterionic Surfactants,” Journal of Or- ganic Chemistry, Vol. 60, No. 17, 1995, pp. 5474-5479. doi:10.1021/jo00122a028
O. R. Gautun, P. H. J. Carlsen, T. Maldal, O. Vikane and E. Gilje, “Selective Synthesis of Aliphatic Ethylene Gly- col Sulfonate Surfactants,” Acta Chemica Scandinavica, Vol. 50, 1996, pp. 170-177. doi:10.3891/acta.chem.scand.50-0170
J. H. Flanagan, S. H. Khan, S. Menchen, S. A. Soper and R. P. Hammer, “Functionalized Tricarbocyanine Dyes as Near-Infrared Fluorescent Probes for Biomolecules,” Bio- conjugate Chemistry, Vol. 8, No. 5, 1997, pp. 751-756. doi:10.1021/bc970113g
G. Carrea, G. Ottolina, S. Riva, B. Danieli, G. Lesma and G. Palmisano, “Alkylation of Adenine, Adenosine, and NAD+ with 1,3-Propanesultone. Synthesis of N6-(3-Sulfo- natopropyl)-NAD+, a New NAD+ Derivative with Sub- stantial Coenzyme Activity,” Helvetica Chimica Acta, Vol. 71, No. 4, 1988, pp. 762-772. doi:10.1002/hlca.19880710411
U. T. Ruegg and J. Rudinger, “Reaction of Cysteine Thiol Groups with 1,3-Propane Sultone: S-3-Sulphopropyl as a Modifying Group for Protein Chemistry,” International Journal of Peptide and Protein Research, Vol. 6, No. 6, 1974, pp. 447-456. doi:10.1111/j.1399-3011.1974.tb02405.x
Y. Ikenoue, Y. Saida, M. Kira, H. Tomozawa, H. Yahima and M. Kobayashi, “A Facile Preparation of a Self-Doped Conducting Polymer,” Journal of the Chemical Society, Chemical Communications, Vol. 23, 1990, pp. 1694-1695. doi:10.1039/c39900001694
S-J. Xiao, S.Brunner and M.Wieland, “Reactions of Sur- face Amines with Heterobifunctional Cross-Linkers Bear- ing both Succinimidyl Ester and Maleimide for Grafting Biomolecules,” Journal of Physical Chemistry B, Vol. 108, No. 42, 2004, pp. 16508-16517. doi:10.1021/jp047726s
S. Riahi, F. Edris-Tabrizi, M. Javanbakht, M. R. Ganjali and P. Norouzi, “A Computational Approach to Studying Monomer Selectivity towards the Template in an Imprinted Polymer,” Journal of Molecular Modeling, Vol. 15, No. 7, 2004, pp. 829-836. doi:10.1007/s00894-008-0437-2
C. Wood, B. Tan, A. Trewin, H. Niu, D. Bradshaw, M. J. Rosseinsky, Y. Z. Khimyak, N. L. Campbell, R. Kirk, E. Stockel and A. I. Cooper, “Hydrogen Storage in Micro- porous Hypercrosslinked Organic Polymer Networks,” Chemistry of Materials, Vol. 19, No. 8, 2007, pp. 2034- 2048. doi:10.1021/cm070356a