Synthesis of poly(amide-thioether) with tunable hydrophilicity via thiolactone chemistry and its application in oil-in-oil emulsions

Zhengzhou Su; Chunmei Li; Jiaojun Tan; Ying Xue; Guoxian Zhang; Yumin Yang; Qiuyu Zhang

doi:10.1016/j.jcis.2019.04.070

Synthesis of poly(amide-thioether) with tunable hydrophilicity via thiolactone chemistry and its application in oil-in-oil emulsions

J Colloid Interface Sci. 2019 Aug 1:549:201-211. doi: 10.1016/j.jcis.2019.04.070. Epub 2019 Apr 23.

Authors

Zhengzhou Su¹, Chunmei Li¹, Jiaojun Tan², Ying Xue¹, Guoxian Zhang¹, Yumin Yang¹, Qiuyu Zhang³

Affiliations

¹ MOE Key Laboratory of Materials Physics and Chemistry under Extraordinary Conditions and Department of Applied Chemistry, School of Science, Northwestern Polytechnical University, Xi'an, China.
² MOE Key Laboratory of Materials Physics and Chemistry under Extraordinary Conditions and Department of Applied Chemistry, School of Science, Northwestern Polytechnical University, Xi'an, China; Key Laboratory of Pulp and Paper Science & Technology of Ministry of Education/Shandong Province, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, China; College of Bioresources Chemical and Materials Engineering, Shaanxi University of Science and Technology, Xi'an, China. Electronic address: tanjiaojun@sust.edu.cn.
³ MOE Key Laboratory of Materials Physics and Chemistry under Extraordinary Conditions and Department of Applied Chemistry, School of Science, Northwestern Polytechnical University, Xi'an, China. Electronic address: qyzhang@nwpu.edu.cn.

PMID: 31039456
DOI: 10.1016/j.jcis.2019.04.070

Abstract

Oil-in-oil emulsions are ideal systems for water-sensitive reactions such as polymerizations and catalytic reactions, which has received extensive attention in recent years. The application of oil-in-oil emulsions has been developed slowly due to the limited types of surfactants and complicated synthesis process. Herein, we proposed a simple method to prepare poly(amide-thioether)-based surfactant for oil-in-oil emulsions via taking advantage of single-pot multicomponent and click characters of thiolactone chemistry. Using a combination of alkyl amine and acrylamide thiolactone, the aminolysis of thiolctone occurred first, generating thiol group in-situ, and then the generated thiol group would sequentially react with the double bonds of acrylamide to form polythioether in the presence of amine. The hydrophobicity of the surfactant could be effectively adjusted by the chain length of the alkyl amine and thus this polymer could serve as a promising surfactant for oil-in-oil emulsion. Notably, the emulsion types could be switched by changing the chain length of the alkyl amine. In addition, the effects of surfactant loading, volume ratio of oil phases, oil types on the size and stability of oil-in-oil emulsions were further investigated. It was demonstrated that the oil-in-oil emulsion stabilized by poly(amide-thioether)s kept stable after more than five months. Besides, we preliminarily explored the application of the oil-in-oil emulsion to prepare closed cell foam and porous particles via photo-initiated thiol-ene polymerization. It is believed that this super-stable oil-in-oil emulsion could offer more possibilities for highly potential water-sensitive systems.

Keywords: Hydrophobicity; Multicomponent; Oil-in-oil emulsion; Poly(amide-thioether); Thiolactone.