基于松油烯的表面活性剂的合成及性能  

Synthesis and properties of terpinene-based surfactants

作　　者：王荣臻 余伟 张丹丹 汪金萍 辛思林 刁开盛 WANG Rongzhen;YU Wei;ZHANG Dandan;WANG Jinping;XIN Silin;DIAO Kaisheng(School of Chemistry and Chemical Engineering,Guangxi Minzu University,Key Laboratory of Chemistry and Engineering of Forest Products,State Ethnic Affairs Commission,Guangxi Key Laboratory of Chemistry and Engineering of Forest Products,Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products,Nanning 530006,Guangxi,China)

机构地区：[1]广西民族大学化学化工学院林产化学与工程国家民委重点实验室广西林产化学与工程重点实验室广西林产化学与工程协同创新中心,广西南宁530006

出　　处：《精细化工》2023年第4期852-860,877,共10页Fine Chemicals

基　　金：国家自然科学基金(22166007)。

摘　　要：以α-松油烯为原料,通过Diels-Alder反应制得1-甲基-4-异丙基双环[2.2.2]-5-辛烯-2-甲酸二甲氨基乙酯(叔胺,TA),再利用产物TA制得1-甲基-4-异丙基双环[2.2.2]-5-辛烯-2-甲酸乙酯-2′-(N,N-二甲基)氧化胺(氧化叔胺,TAO)、1-甲基-4-异丙基双环[2.2.2]-5-辛烯-2-甲酸乙酯-2′-(N,N-二甲基-N-苄基)氯化铵(苄氯季铵盐,TABC)和1-甲基-4-异丙基双环[2.2.2]-5-辛烯-2-甲酸乙酯-2′-(N,N,N-三甲基)碘化铵(碘甲基季铵盐,TAMI)3种表面活性剂;采用FTIR及1HNMR对产物进行了结构表征,并考察了3种表面活性剂的表面性能和抑菌性能。结果发现,TAO、TABC和TAMI的临界胶束浓度(CMC)分别为3.39×10^(-3)、2.46×10^(-3)和2.37×10^(-3)mol/L,临界胶束浓度下的表面张力(γCMC)分别为33.0、25.2和26.4 mN/m,比商品化表面活性剂十二烷基二甲基苄基氯化铵的CMC和γCMC更低;TAO、TABC和TAMI具有良好的乳化能力,乳化时间分别为581.0、341.7和271.0 s。TABC和TAMI的0 min起泡高度可达76.62和82.77 mm,并且二者稳泡性能可达到0.85和0.87;此外,TABC和TAMI具有很好的钙硬水稳定性,而TAO的钙硬水稳定性较差。TABC对金黄色葡萄球菌的抑菌活性最好,抑菌圈直径为21 mm,抑菌率可达99.99%。Three surfactants of 4-isopropyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid ethyl ester-2'-(N,N-dimethyl)amine oxide(tertiary amine N-oxide,TAO),4-isopropyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid ethyl ester-2'-(N,N-dimethyl-N-benzyl)ammonium chloride(tertiary amine N-benzyl chloride,TABC),and 4-isopropyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid ethyl ester-2'-(N,N,N-trimethyl)ammonium iodide(tertiary amine N-methyl iodide,TAMI)were derived from 2-(dimethylamino)ethyl 4-isopropyl-1-methylbicyclo[2.2.2]oct-5-ene-2-carboxylate(tertiary amine,TA)which was synthesized fromα-terpinene by Diels-Alder reaction.The three surfactants were then characterized by FTIR and 1HNMR,followed by investigation on their surface properties and bacteriostatic abilities.The results showed that the critical micelle concentration(CMC)of TAO,TABC and TAMI was 3.39×10^(-3),2.46×10^(-3) and 2.37×10^(-3) mol/L,and the corresponding surface tension(γCMC)was 33.0,25.2 and 26.4 mN/m,respectively,lower than those of commercial analogue dodecyl dimethyl benzyl ammonium chloride(DDBAC).Moreover,TAO,TABC and TAMI exhibited good emulsification property with emulsifying time of 581.0,341.7 and 271.0 s,respectively,as well as good foaming performance and foam stability with a foaming height of 76.62 and 82.77 mm,and the foaming stability of 0.85 and 0.87,respectively.In addition,TABC and TAMI perform well in calcium hard water stability test,while TAO in calcium hard water stability test is unstable.Furthermore,TABC shows the best bacteriostatic effect on Staphylococcus aureus,with 21 mm in the diameter of bacteriostatic zone and 99.99%in the bacteriostatic rates.

关 键 词：α-松油烯 氧化胺 季铵盐 表面活性剂 表面性能 抑菌性 

分 类 号：TQ423[化学工程]