松香基胆碱季铵盐表面活性剂的合成及抑菌活性研究

Synthesis and Antibacterial Activity of Rosinyl Choline Quaternary Ammonium Surfactants

以脱氢枞酸、脱氢枞胺马来酸、丙烯海松酸、马来海松酸为原料,分别与胆碱反应合成了4种松香基胆碱季铵盐表面活性剂（Ⅰ1~Ⅳ1）,同时分别与四甲基氢氧化铵反应合成了4种不含羟基松香基四甲基氢氧化铵季铵盐表面活性剂（Ⅰ2~Ⅳ2）。采用IR、1H NMR及13C NMR表征了产物的结构,并对其临界胶束浓度（CMC）、表面张力（γCMC）、乳化性能、泡沫性能、亲水亲油平衡值（HLB）等表面活性及抑菌性能进行了研究。结果表明,Ⅰ1、Ⅱ1、Ⅲ1和Ⅳ1的CMC值为6.9、2.0、3.8和8.0 mmol/L,对应γCMC为37.9、35.1、40.0和42.4 m N/m;Ⅰ2、Ⅱ2、Ⅲ2和Ⅳ2的CMC值为9.4、5.2、6.2和10.0 mmol/L,对应γCMC为39.7、39.0、43.1和45.1 m N/m。通过比较可知,带有羟基的季铵盐表面活性剂的CMC值和γCMC均小于相应不含羟基的季铵盐表面活性剂,说明羟基的存在能够提高表面活性剂的表面活性。8种松香基季铵盐表面活性剂的HLB值均大于18,具有较好的亲水性。表面活性剂Ⅱ1起泡性较好,起泡高度达到202 mm,5 min后对应的泡沫高度为165 mm。季铵盐Ⅲ1、Ⅲ2、Ⅳ1和Ⅳ2对表皮葡萄球菌具有良好的抑制效果,最小抑菌浓度为2 mg/L,优于市售的新洁尔灭和氨苄青霉素钠。羟基的存在对松香基季铵盐的抑菌性能无明显影响。

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,13 C 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,Ⅳ1were 6. 9,2. 0,3. 8 and 8. 0 mmol / L,the correspondingγCMCvalues were 37. 9,35. 1,40. 0 and 42. 4 m N / m. The CMC values of Ⅰ2,Ⅱ2,Ⅲ2,Ⅳ2were 9. 4,5. 2,6. 2 and10. 0 mmol / L,the corresponding γCMCvalues were 39. 7,39. 0,43. 1 and 45. 1 m N / m. By comparison,CMC values and γCMCofquaternary 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 Ⅱ1was better than the others,and foaming height was 202 mm,and then it turned to165 mm after 5 min. Ⅲ1,Ⅲ2,Ⅳ1and Ⅳ2exhibited 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.