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

Rui Wang, Yuna Luo, Chuan-Jie Cheng, Qing-Hua Huang, Hua-Shan Huang, Shuang-Lin Qin, and Yuan-Ming Tu

Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Fenglin Street, Nanchang, Jiangxi 330013, PR China

 

E-mail: chengcj530@163.com

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.

Keywords: cationic surfactant – cardanol – emulsion polymerisation – renewable resource – ATRP

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2016-0052

 

Chemical Papers 70 (9) 1218–1227 (2016)

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