新型生物基超长链阳离子表面活性剂的合成及其表面活性

Synthesis and Surface Activities of A Novel Bio-based Ultralong Chain Cationic Surfactant

以油酸为原料,与无水甲醇经酯化反应制得油酸甲酯( 1 );1 经还原和取代反应制得1-氯-顺式-9-十八烯( 3 );3 与对羟基苯甲醛经取代反应制得( E )-4-(十八碳-9-烯-1-基氧基)苯甲醛( 4 );4 依次经取代、还原及酸化反应合成了一种新型伯胺盐阳离子表面活性剂( E )-[4-(十八碳-9-烯-1-基氧基)苯基]甲烷氯化铵( 7 ),总收率25.35%,其结构经 1 H NMR和IR表征。采用表面张力法研究了 7 的表面活性。结果表明: 7 具有较强的聚集能力和界面吸附能力,其 cmc ,γ cmc ,Γ max 和 Amin 分别为0.251mmol·L^-1,28.8 mN·m^-1,2.41 μmol·m^-2 和0.69nm^2 。

Methyl oleate( 1 ) was obtained by esterification from oleic acid with anhydrous methanol. 1-Chloro- cis -9-octadecene( 3 ) was prepared by reduction and substitution from 1 . A novel primary amine salt cationic surfactant,( E )-[4-(octadec-9-en-1-yloxy) phenyl] methanaminium chloride( 7 ), with the overall yield of 25.35%, was synthesized through substitution, reduction and acidification from( 4 ) which was prepared by substitution of hydroxybenzaldehyde with 3 . The structure was characterized by 1 H NMR and IR. The surface activities of 7 were investigated by surface tension method. The results showed that 7 exhibited strong aggregation and adsorption ability with cmc =0.251 mmol·L^-1 ,γ cmc =28.8 mN·m^-1 ,Γ max =2.41 μmol·m^-2 and A min =0.69 nm^2 .