Startseite Syntheses of cardanol-based cationic surfactants and their use in emulsion polymerisation
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Syntheses of cardanol-based cationic surfactants and their use in emulsion polymerisation

  • Rui Wang , Yuna Luo , Chuan-Jie Cheng EMAIL logo , Qing-Hua Huang , Hua-Shan Huang , Shuang-Lin Qin und Yuan-Ming Tu
Veröffentlicht/Copyright: 22. April 2016
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Abstract

Six quaternary ammonium salts were designed and synthesised with moderate to high yields in three steps, based on cardanol, a low-cost and abundant renewable resource. The new ammonium salts can act as reactive surfactants due to their having both a hydrophilic ammonium group and a hydrophobic unsaturated alkyl chain. The gemini surfactants with a linker of a linear saturated aliphatic hydrocarbon chain exhibited a relatively low CMC value(≤ 0.2 mmol L−1) and surface tension (≤ 27 mN m−1), signifying that this kind of amphiphile exhibited good surface active properties. The photo-active gemini surfactant with critical micelle concentration (CMC)of 0.05mmolL−1 was used successfully as the sole emulsifier in the emulsion polymerization of methyl methacrylate (MMA).In addition, abenzyl bromide-containing surfactant can act as both an atom transfer radical polymerization (ATRP) initiator and an emulsifier in an activator generated by the electron transfer atom transfer radical polymerization (AGET ATRP) of MMA in emulsion. The value of the number-average molecular mass of the resulting cardanol-endpoly (methyl methacrylate) (PMMA) is Mn, GPC = 45.1 kDa, with polydispersity of 1.39.

Acknowledgements

This work was financially supported by the Natural Science Foundations of China (nos. 21264008 and 21564004), the 8th Foundation of Creativity and Study for College Students in Jiangxi Science and Technology Normal University.

References

Alswieleh, A. M., Cheng, N., Canton, I., Ustbas, B., Xue, X., Ladmiral, V., Xia, S. J., Ducker, R. E., Zubir, O. E., Cartron, M. L., Hunter, C. N., Leggett, G. J., & Armes, S. P. (2014). Zwitterionic poly(amino acid methacrylate) brushes. Journal of the American Chemical Society, 136, 9404–9413. DOI: 10.1021/ja503400r.10.1021/ja503400rSuche in Google Scholar PubMed PubMed Central

Bai, L. J., Zhang, L. F., Cheng, Z. P., & Zhu, X. L. (2012). Activators generated by electron transfer for atom transfer radical polymerisation: recent advances in catalyst and polymer chemistry. Polymer Chemistry, 3, 2685–2697. DOI: 10.1039/c2py20286g.10.1039/c2py20286gSuche in Google Scholar

Balachandran, V. S., Jadhav, S. R., Vemula, P. K., & John, G. (2013). Recent advances in cardanol chemistry in a nutshell: from a nut to nanomaterials. Chemical Society Review, 42, 427–438. DOI: 10.1039/c2cs35344j.10.1039/c2cs35344jSuche in Google Scholar PubMed

Bhavsar, G. A., & Asha, S. K. (2011). Pentadecyl phenoland cardanol-functionalized fluorescent, room-temperature liquid-crystalline perylene bisimides: Effect of pendant chain unsaturation on self-assembly. Chemistry, A European Journal, 17, 12646–12658. DOI: 10.1002/chem.201101011.10.1002/chem.201101011Suche in Google Scholar PubMed

Bloise, E., Becerra-Herrera, M., Mele, G., Sayago, A., Carbone, L., D’Accolti, L., Mazzetto, S. E., & Vasapollo, G. (2014). Sustainable preparation of cardanol-based nanocarriers with embedded natural phenolic compounds. ACS Sustainable Chemistry & Engineering, 2, 1299–1304. DOI: 10.1021/sc500123r.10.1021/sc500123rSuche in Google Scholar

Bombelli, C., Giansanti, L., Luciani, P., & Mancini, G. (2009). Gemini surfactant based carriers in gene and drug delivery. Current Medicinal Chemistry, 16, 171–183. DOI: 10.2174/092986709787002808.10.2174/092986709787002808Suche in Google Scholar PubMed

Brown, P., Butts, C. P., & Eastoe, J. (2013). Stimuliresponsive surfactants. Soft Matter, 9, 2365–2374. DOI: 10.1039/c3sm27716j.10.1039/c3sm27716jSuche in Google Scholar

Chen, G. Q., & Patel, M. K. (2012). Plastics derived from biological sources: Present and future: A technical and environmental review. Chemical Reviews, 112, 2082–2099. DOI: 10.1021/cr200162d.10.1021/cr200162dSuche in Google Scholar PubMed

Cheng, C. J., Shu, J. B., Gong, S. S., Shen, L., Qiao, Y. L., & Fu, C. Q. (2010). Synthesis and use of a surface-active initiator in emulsion polymerization under AGET and ARGET ATRP conditions. New Journal of Chemistry, 34, 163–170. DOI: 10.1039/b9nj00307j.10.1039/b9nj00307jSuche in Google Scholar

Cheng, C. J., Bai, X. X., Liu, S. J., Huang, Q. H., Tu, Y. M., Wu, H. M., & Wang, X. J. (2013a). UV cured polymer based on a renewable cardanol derived RAFT agent. Journal of Polymer Research, 20, 197. DOI: 10.1007/s10965-013-0197-2.10.1007/s10965-013-0197-2Suche in Google Scholar

Cheng, C. J., Fu, Q. L., Bai, X. X., Liu, S. J., Shen, L., Fan, W. Q., & Li, H. X. (2013b). Facile synthesis of gemini surface-active ATRP initiator and its use in soap-free AGET ATRP mini-emulsion polymerization. Chemical Papers, 67, 336–341. DOI: 10.2478/s11696-012-0271-y.10.2478/s11696-012-0271-ySuche in Google Scholar

Cheng, C. J., Bai, X. X., Fan, W. Q., Wu, H. M., Shen, L., Huang, Q. H., & Tu, Y. M. (2014). Synthesis of a photoactive gemini surfactant and its use in AGET ATRP miniemulsion polymerisation and UV curing. Chemical Papers, 68, 136–144. DOI: 10.2478/s11696-013-0420-y.10.2478/s11696-013-0420-ySuche in Google Scholar

Cheng, C. J., Zhang, X., Bai, X. X., Li, J., Cao, X. X., & Wang, J. L. (2015). Synthesis of cardanol-based photoactive SET-LRP initiator and its application to preparation of UV-cured resin. Chemical Papers, 69, 1608–1616. DOI: 10.1515/chempap-2015-0176.10.1515/chempap-2015-0176Suche in Google Scholar

Deng, W. X., Zhang, Y. C., Zhong, Y. W., & Peng, J. W. (2014). Synthesis and thermodynamic properties of rosinbased cationic gemini surfactants. Journal of Surfactants and Detergents, 17, 453–458. DOI: 10.1007/s11743-013-1559-9.10.1007/s11743-013-1559-9Suche in Google Scholar

Hu, J. W., Zhang, X. Y., & Wang, Z. W. (2010). A review on progress in QSPR studies for surfactants. International Journal of Molecular Sciences, 11, 1020–1047. DOI: 10.3390/ijms11031020.10.3390/ijms11031020Suche in Google Scholar PubMed PubMed Central

Iwata, T. (2015). Biodegradable and bio-based polymers: Future prospects of eco-friendly plastics. Angewandte Chemie International Edition, 54, 3210–3215. DOI: 10.1002/anie.201410770.10.1002/anie.201410770Suche in Google Scholar PubMed

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, 7762–7773. DOI: 10.1021/jo9018107.10.1021/jo9018107Suche in Google Scholar PubMed

Kaewprapan, K., Baros, F., Marie, E., Inprakhon, P., & Durand, A. (2012). Macromolecular surfactants synthesized by lipase-catalyzed transesterification of dextran with vinyl decanoate. Carbohydrate Polymer, 88, 313–320. DOI: 10.1016/j.carbpol.2011.12.010.10.1016/j.carbpol.2011.12.010Suche in Google Scholar

Korth, B. D., Keng, P., Shim, I., Bowles, S. E., Tang, C., Kowalewski, T., Nebesny, K.W., & Pyun, J. (2006). Polymercoated ferromagnetic colloids from well-defined macromolecular surfactants and assembly into nanoparticle chains. Journal of the American Chemical Society, 128, 6562–6563. DOI 10.1021/ja0609147.10.1021/ja0609147Suche in Google Scholar PubMed

Lebarbé, T., Grau, E., Gadenne, B., Alfos, C., & Cramail, H. (2015). Synthesis of fatty acid-based polyesters and their blends with poly(l-lactide) as a way to Tailor PLLA toughness. ACS Sustainable Chemistry & Engineering, 3, 283–292. DOI: 10.1021/sc500648g.10.1021/sc500648gSuche in Google Scholar

Matyjaszewski, K. (2012). Atom transfer radical polymerization (ATRP): Current status and future perspectives. Macromolecules, 45, 4015–4039. DOI: 10.1021/ma3001719.10.1021/ma3001719Suche in Google Scholar

Mele, G., & Vasapollo, G. (2008). Fine chemicals and new hybrid materials from cardanol. Mini-Reviews in Organic Chemistry, 5, 243–253. DOI: 10.2174/157019308785161611.10.2174/157019308785161611Suche in Google Scholar

Miyake, G. M., & Theriot, J. C. (2014). Perylene as an organic photocatalyst for the radical polymerization of functionalized vinyl monomers through oxidative quenching with alkyl bromides and visible light. Macromolecules, 47, 8255–8261. DOI: 10.1021/ma502044f.10.1021/ma502044fSuche in Google Scholar

Pan, X. C., Lamson, M., Yan, J. J., & Matyjaszewski, K. (2015). Photoinduced metal-free atom transfer radical polymerization of acrylonitrile. ACS Macro Letters, 4, 192–196. DOI: 10.1021/mz500834g.10.1021/mz500834gSuche in Google Scholar PubMed

Singh, H., Balamurugan, A., & Jayakannan, M. (2013). Solid state assemblies and photophysical characteristics of linear and bent-core πconjugated oligophenylenevinylenes. ACS Applied Materials & Interfaces, 5, 5578–5591. DOI: 10.1021/ am400868e.10.1021/ am400868eSuche in Google Scholar

Suresh, K. I. (2013). Rigid polyurethane foams from cardanol: Synthesis, structural characterization, and evaluation of polyol and foam properties. ACS Sustainable Chemistry & Engineering, 1, 232–242. DOI: 10.1021/sc300079z.10.1021/sc300079zSuche in Google Scholar

Takahashi, Y., Fukuyasu, K., Horiuchi, T., Kondo, Y., & Stroeve, P. (2014). Photoinduced demulsification of emulsions using a photoresponsive gemini surfactant. Langmuir, 30, 41–47. DOI: 10.1021/la4034782.10.1021/la4034782Suche in Google Scholar PubMed

Tasdelen, M. A., Kahveci, M. U., & Yagci, Y. (2011). Telechelic polymers by living and controlled/living polymerization methods. Progress in Polymer Science, 36, 455–567. DOI: 10.1016/j.progpolymsci.2010.10.002.10.1016/j.progpolymsci.2010.10.002Suche in Google Scholar

Treat, N. J., Sprafke, H., Kramer, J. W., Clark, P. G., Barton, B. E., de Alaniz, J. R., Fors, B. P., & Hawker, C. J. (2014). Metal-free atom transfer radical polymerization. Journal of the American Chemical Society, 136, 16096–16101. DOI: 10.1021/ja510389m.10.1021/ja510389mSuche in Google Scholar PubMed

Voirin, C., Caillol, S., Sadavarte, N. V., Tawade, B. V., Boutevin, B., & Wadgaonkar, P. P. (2014). Functionalization of cardanol: towards biobased polymers and additives. Polymer Chemistry, 5, 3142–3162. DOI: 10.1039/c3py01194a.10.1039/c3py01194aSuche in Google Scholar

Yamago, S., & Nakamura, Y. (2013). Recent progress in the use of photoirradiation in living radical polymerization. Polymer, 54, 981–994. DOI: 10.1016/j.polymer.2012.11.046.10.1016/j.polymer.2012.11.046Suche in Google Scholar

Yao, K. J., & Tang, C. B. (2013). Controlled polymerization of next-generation renewable monomers and beyond. Macromolecules, 46, 1689–1712. DOI: 10.1021/ma3019574.10.1021/ma3019574Suche in Google Scholar

Yu, J., Liu, Y. P., Liu, X. H., Wang, C. P., Wang, J. F., Chu, F. X., & Tang, C. B. (2014). Integration of renewable cellulose and rosin towards sustainable copolymers by “grafting from” ATRP. Green Chemistry, 16, 1854–1864. DOI: 10.1039/c3gc41550c.10.1039/c3gc41550cSuche in Google Scholar

Received: 2015-10-30
Revised: 2016-1-25
Accepted: 2016-1-29
Published Online: 2016-4-22
Published in Print: 2016-9-1

© 2016 Institute of Chemistry, Slovak Academy of Sciences

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