Synthesis of a photoactive gemini surfactant and its use in AGET ATRP miniemulsion polymerisation and UV curing

详细信息    查看全文

• 作者：Chuan-Jie Cheng (1)
  Xiong-Xiong Bai (1)
  Wu-Qin Fan (1)
  Hai-Ming Wu (1)
  Liang Shen (1)
  Qing-Hua Huang (1)
  Yuan-Ming Tu (1)
  
• 关键词：gemini surfactant ; photoinitiator ; activator generated by electron transfer atom transfer radical polymerisation (AGET ATRP) ; miniemulsion polymerisation ; soap ; free
• 刊名：Chemical Papers
• 出版年：2014
• 出版时间：January 2014
• 年：2014
• 卷：68
• 期：1
• 页码：136-144
• 全文大小：320KB
• 参考文献：1. Bai, L., Zhang, L., Zhang, Z., Zhu, J., Zhou, N., Cheng, Z., & Zhu, X. (2011). Alumina additives for fast iron-mediated AGET ATRP of MMA using onium salt as ligand. / Journal of Polymer Science Part A: Polymer Chemistry, / 49, 3970鈥?979. DOI: 10.1002/pola.24837. CrossRef
  2. Bai, L., Zhang, L., Cheng, Z., & Zhu, X. (2012). Activators generated by electron transfer for atom transfer radical polymerization: recent advances in catalyst and polymer chemistry. / Polymer Chemistry, / 3, 2685鈥?697. DOI: 10.1039/c2py20286g. CrossRef
  3. Basinska, T., & Slomkowski, S. (2012). Design of polyglycidolcontaining microspheres for biomedical applications. / Chemical Papers, / 66, 352鈥?68. DOI: 10.2478/s11696-011-0122-2. CrossRef
  4. Benoit, D. S. W., Srinivasan, S., Shubin, A. D., & Stayton, P. S. (2011). Synthesis of folate-functionalized RAFT polymers for targeted siRNA delivery. / Biomacromolecules, / 12, 2708鈥?714. DOI: 10.1021/bm200485b. CrossRef
  5. Brandt, W. C., de Oliveira Tomaselli, L., Correr-Sobrinho, L., & Sinhoreti, M. A. C. (2011). Can phenyl-propanedione influence Knoop hardness, rate of polymerization and bond strength of resin composite restorations? / Journal of Dentistry, / 39, 438鈥?47. DOI: 10.1016/j.jdent.2011.03.009. CrossRef
  6. Braunecker, W. A., & Matyjaszewski, K. (2007). Controlled/living radical polymerization: Features, developments, and perspectives. / Progress in Polymer Science, / 32, 93鈥?46. DOI: 10.1016/j.progpolymsci.2006.11.002. CrossRef
  7. Chen, Z., Wu, J., Fernando, S., & Jagodzinski, K. (2011). Soy-based, high biorenewable content UV curable coatings. / Progress in Organic Coatings, / 71, 98鈥?09. DOI: 10.1016/j.porgcoat.2011.01.004. CrossRef
  8. Cheng, C., Shu, J., Gong, S., Shen, L., Qiao, Y., & Fu, C. (2010). Synthesis and use of a surface-active initiator in emulsion polymerization under AGET and ARGET ATRP conditions. / New Journal of Chemistry, / 34, 163鈥?70. DOI: 10.1039/b9nj00307j. CrossRef
  9. Cheng, C., Shen, L., Fu, Q., & Gong, S. (2011a). Soap-free living/controlled radical emulsion polymerization. / Progress in Chemistry, / 23, 791鈥?99. (in Chinese)
  10. Cheng, C., Fu, Q., Liu, Z., Shen, L., Qiao, Y., & Fu, C. (2011b). Emulsifier-free synthesis of crosslinkable ABA triblock copolymer nanoparticles / via AGET ATRP. / Macromolecular Research, / 19, 1048鈥?055. DOI: 10.1007/s13233-011-1008-4. CrossRef
  11. Cheng, C. J., Fu, Q. L., Bai, X. X., Liu, S. J., Shen, L., Fan, W. Q., & Li, H. X. (2013). Facile synthesis of gemini surfaceactive ATRP initiator and its use in soap-free AGET ATRP mini-emulsion polymerisation. / Chemical Papers, / 67, 336鈥?41. DOI: 10.2478/s11696-012-0271-y. CrossRef
  12. Chu, D. S. H., Schellinger, J. G., Shi, J., Convertine, A. J., Stayton, P. S., & Pun, S. H. (2012). Application of living free radical polymerization for nucleic acid delivery. / Accounts of Chemical Research, / 45, 1089鈥?099. DOI: 10.1021/ar200242z. CrossRef
  13. Destarac, M. (2010). Controlled radical polymerization: Industrial stakes, obstacles and achievements. / Macromolecular Reaction Engineering, / 4, 165鈥?79. DOI: 10.1002/mren.200900087. CrossRef
  14. Eriksson, M., Boyer, A., Sinigoi, L., Johansson, M., Malmstr枚m, E., Hult, K., Trey, S., & Martinelle, M. (2010). One-pot enzymatic route to tetraallyl ether functional oligoesters: Synthesis, UV curing, and characterization. / Journal of Polymer Science Part A: Polymer Chemistry, / 48, 5289鈥?297. DOI: 10.1002/pola.24328. CrossRef
  15. Jahan, N., Paul, N., Petropolis, C. J., Marangoni, D. G., & Grindley, T. B. (2009). Synthesis of surfactants based on pentaerythritol. / I. Cationic and zwitterionic gemini surfactants. The Journal of Organic Chemistry, / 74, 7762鈥?773. DOI: 10.1021/jo9018107.
  16. Jakubowski, W., & Matyjaszewski, K. (2005). Activator generated by electron transfer for atom transfer radical polymerization. / Macromolecules, / 38, 4139鈥?146. DOI: 10.1021/ma0 47389l. CrossRef
  17. Jiang, H., Zhang, L., Pan, J., Jiang, X., Cheng, Z., & Zhu, X. (2012). Iron-mediated AGET ATRP of methyl methacrylate using metal wire as reducing agent. / Journal of Polymer Science Part A: Polymer Chemistry, / 50, 2244鈥?253. DOI: 10.1002/pola.26002. CrossRef
  18. Li, W., Matyjaszewski, K., Albrecht, K., & M枚ller, M. (2009). Reactive surfactants for polymeric nanocapsules via interfacially confined miniemulsion ATRP. / Macromolecules, / 42, 8228鈥?233. DOI: 10.1021/ma901574y. CrossRef
  19. Lin, J., Wang, W., Wen, X., Cai, Z. Q., Pi, P., Zheng, D. F., Cheng, J., & Yang, Z. (2012). Thermal stability, curing kinetics and properties of polyurethanes system for in-mould decoration ink. / Pigment & Resin Technology, / 41, 351鈥?58. DOI: 10.1108/03699421211274270. CrossRef
  20. Lindstr枚m, U. M. (Ed.) (2007). / Organic reactions in water: Principles, strategies and applications. Oxford, UK: Blackwell Publishing.
  21. Lou, Q., & Shipp, D. A. (2012). Recent developments in atom transfer radical polymerization (ATRP): Methods to reduce metal catalyst concentrations. / ChemPhysChem, / 13, 3257鈥?261. DOI: 10.1002/cphc.201200166. CrossRef
  22. Matyjaszewski, K. (2012). Atom transfer radical polymerization (ATRP): Current status and future perspectives. / Macromolecules, / 45, 4015鈥?039. DOI: 10.1021/ma3001719. CrossRef
  23. Miao, J., Jiang, H., Zhang, L., Wu, Z., Cheng, Z., & Zhu, X. (2012). AGET ATRP of methyl methacrylate / via a bimetallic catalyst. / RSC Advances, / 2, 840鈥?47. DOI: 10.1039/c1ra00456e. CrossRef
  24. Mincheva, R., Paneva, D., Mespouille, L., Manolova, N., Rashkov, I., & Dubois, P. (2009). Optimized water-based ATRP of an anionic monomer: Comprehension and properties characterization. / Journal of Polymer Science Part A: Polymer Chemistry, / 47, 1108鈥?119. DOI: 10.1002/pola.23 222. CrossRef
  25. Oh, J. K., Perineau, F., Charleux, B., & Matyjaszewski, K. (2009). AGET ATRP in water and inverse miniemulsion: A facile route for preparation of high-molecular-weight biocompatible brush-like polymers. / Journal of Polymer Science Part A: Polymer Chemistry, / 47, 1771鈥?781. DOI: 10.1002/pola.23272. CrossRef
  26. Shen, L., Ma, C., Pu, S., Cheng, C., Xu, J., Li, L., & Fu, C. (2009). Synthesis and properties of novel photochromic poly(methyl methacrylate-co-diarylethene)s. / New Journal of Chemistry, / 33, 825鈥?30. DOI: 10.1039/b813901f. CrossRef
  27. Shu, J., Cheng, C., Zheng, Y., Shen, L., Qiao, Y., & Fu, C. (2011). 鈥淥ne pot鈥?synthesis of fluorinated block copolymers using a surface-active ATRP initiator under emulsion polymerization conditions. / Polymer Bulletin, / 67, 1185鈥?200. DOI: 10.1007/s00289-011-0446-7. CrossRef
  28. Tsujii, Y., Ohno, K., Yamamoto, S., Goto, A., & Fukuda, T. (2006). Structure and properties of high-density polymer brushes prepared by surface-initiated living radical polymerization. In R. Jordan (Ed.), / Surface-initiated polymerization I (Advances in polymer science series, Vol. 197, pp. 1鈥?5). Berlin, Germany: Springer. DOI: 10.1007/12 063. CrossRef
  29. Tasdelen, M. A., Kahveci, M. U., & Yagci, Y. (2011). Telechelic polymers by living and controlled/living polymerization methods. / Progress in Polymer Science, / 36, 455鈥?67. DOI: 10.1016/j.progpolymsci.2010.10.002. CrossRef
  30. Wang, H., Pan, Q., & Rempel, G. L. (2012). Organic solventfree catalytic hydrogenation of diene-based polymer nanoparticles in latex form: Part I. / Preparation of nano-substrate. Journal of Polymer Science Part A: Polymer Chemistry, / 50, 4656鈥?665. DOI: 10.1002/pola.26277. CrossRef
  31. Yagci, Y., Jockusch, S., & Turro, N. J. (2010). Photoinitiated polymerization: Advances, challenges, and opportunities. / Macromolecules, / 43, 6245鈥?260. DOI: 10.1021/ma1007545. CrossRef
  32. Yan, Q., Zhou, R., Fu, C., Zhang, H., Yin, Y., & Yuan, J. (2011). CO2-responsive polymeric vesicles that breathe. / Angewandte Chemie International Edition, / 50, 4923鈥?927. DOI: 10.1002/anie.201100708. CrossRef
  33. Yilmaz, G., Beyazit, S., & Yagci, Y. (2011). Visible light induced free radical promoted cationic polymerization using thioxanthone derivatives. / Journal of Polymer Science Part A: Polymer Chemistry, / 49, 1591鈥?596. DOI: 10.1002/pola.24582. CrossRef
  34. Zana, R. (2002). Dimeric and oligomeric surfactants. Behavior at interfaces and in aqueous solution: a review. / Advances in Colloid and Interface Science, / 97, 205鈥?53. DOI: 10.1016/s0001-8686(01)00069-0. CrossRef
  35. Zhai, S., Shang, J., Yang, D., Wang, S., Hu, J., Lu, G., & Huang, X. (2012). Successive SET-LRP and ATRP synthesis of ferrocene-based PPEGMEA- / g-PAEFC welldefined amphiphilic graft copolymer. / Journal of Polymer Science Part A: Polymer Chemistry, / 50, 811鈥?20. DOI: 10.1002/pola.25836. CrossRef
  36. Zhang, Y., Li, C., & Liu, S. (2009). One-pot synthesis of ABC miktoarm star terpolymers by coupling ATRP, ROP, and click chemistry techniques. / Journal of Polymer Science Part A: Polymer Chemistry, / 47, 3066鈥?077. DOI: 10.1002/pola.23388. CrossRef
  37. Zheng, Y., Cheng, C. J., Huang, H. Q., Shen, L., Fu, C. Q., & Qiao, Y. L. (2011). Fast synthesis of ATRP initiators with photoinitiating activity by urea hydrogen peroxide method. / Chinese Journal of Synthetic Chemistry, / 19, 376鈥?78. (in Chinese)
  38. Zhou, J., & Cui, Y. (2001). Measurement and calculation of HLB value of surfactants. I. The measurement of HLB value. / Speciality Petrochemicals, / 2001, 11鈥?4. (in Chinese)
  39. Zhu, X., Zhou, N., Zhang, Z., Sun, B., Yang, Y., Zhu, J., & Zhu, X. (2011). Cyclic polymers with pendent carbazole units: enhanced fluorescence and redox behavior. / Angewandte Chemie International Edition, / 50, 6615鈥?618. DOI: 10.1002/anie.201101303. CrossRef
  
• 作者单位：Chuan-Jie Cheng (1)
  Xiong-Xiong Bai (1)
  Wu-Qin Fan (1)
  Hai-Ming Wu (1)
  Liang Shen (1)
  Qing-Hua Huang (1)
  Yuan-Ming Tu (1)
  
  1. Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Fenglin Street, Nanchang, Jiangxi, 330013, China
  
• ISSN：1336-9075

文摘

A novel photoactive gemini surfactant was easily synthesised in high yields. The multi-functional molecule can be used as a gemini surfactant, a benzophenone type photoinitiator, and as an ATRP initiator. Poly(methyl methacrylate) (PMMA) and poly(methyl methacrylate)-block-poly(allyl methacrylate) (PMMA-b-PAMA) were prepared using the photoactive gemini surfactant as an ATRP initiator under soap-free miniemulsion polymerisation conditions. Kinetic results of the miniemulsion polymerisation of methyl methacrylate (MMA) indicate that the reaction has controlled/living characteristics. UV curing was performed by irradiation of the linear PMMA-b-PAMA polymer, in which PMMA-b-PAMA containing a benzophenone moiety functioned as a macromolecular photoinitiator.