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Chemistry and Industry of Forest Products ›› 2015, Vol. 35 ›› Issue (5): 98-104.doi: 10.3969/j.issn.0253-2417.2015.05.016

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Synthesis and Antibacterial Activity of Rosinyl Choline Quaternary Ammonium Surfactants

ZHENG Jian-qiang1, LIU Li1, RAO Xiao-ping1,2, SONG Zhan-qian1, SHANG Shi-bin1,2   

  1. 1. Institute of Chemical Industry of Forest Products, CAF;National Engineering Lab.for Biomass Chemical Utilization;Key and Open Lab.of Forest Chemical Engineering, SFA;Key Lab.of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China;
    2. Research Institute of Forestry New Technology, CAF, Beijing 100091, China
  • Received:2014-11-20 Online:2015-10-25 Published:2015-10-24

Abstract: Choline was reacted with dehydroabietic acid, N-(dehydroabietyl)maleamic acid, acrylopimaric acid and maleopimaric acid, respectively, to prepare four rosinyl choline quaternary ammonium surfactants(Ⅰ1-Ⅳ1). And tetramethyl ammonium hydroxide was reacted with the four compounds respectively to prepare four rosinyl quaternary ammonium surfactants without hydroxyl groups (Ⅰ2-Ⅳ2). Their structures were characterized by IR, 1H NMR, 13C NMR spectra. Their critical micelle concentration (CMC), surface tension (γCMC), emulsifying ability, foaming ability, HLB value and bactericidal activity were evaluated. The results showed that CMC values of Ⅰ1, Ⅱ1, Ⅲ1, Ⅳ1 were 6.9, 2.0, 3.8 and 8.0 mmol/L, the corresponding γCMC values were 37.9, 35.1, 40.0 and 42.4 mN/m. The CMC values of Ⅰ2, Ⅱ2, Ⅲ2, Ⅳ2 were 9.4, 5.2, 6.2 and 10.0 mmol/L, the corresponding γCMC values were 39.7, 39.0, 43.1 and 45.1 mN/m. By comparison, CMC values and γCMC of quaternary ammonium salt surfactants with hydroxy groups were smaller than those of quaternary ammonium salt surfactants without hydroxyl groups. It could be seen that the existence of the hydroxyl groups could improve the surface activities of surfactants. HLB values of eight rosin-based quaternary ammonium salts were greater than 18. This showed that they had good hydrophilicity. The foaming ability of Ⅱ1 was better than the others, and foaming height was 202 mm, and then it turned to 165 mm after 5 min. Ⅲ1, Ⅲ2, Ⅳ1 and Ⅳ2 exhibited excellent antibacterial activity against Staphyloccocus epidermidis with minimum inhibition concentration of 2 mg/L, and the antibacterial activities were superior to the Bromogeramine and Ampicillin sodium. It showed that the existence of hydroxyl groups did not affect antibacterial activities of rosin-based quaternary ammonium salt.

Key words: rosin, choline, surfactant, antibacterial activity

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