A series of N-acetylated cationic gemini surfactants (3a-e) having dimeric structures derived from tertiary amines were synthesized. Their antifungal potency and surface properties were determined. It also studied the...A series of N-acetylated cationic gemini surfactants (3a-e) having dimeric structures derived from tertiary amines were synthesized. Their antifungal potency and surface properties were determined. It also studied the acute toxicity of the molecule with the best performance and the best water solubility (3e) through Chlorella vulgaris and Daphnia magna bioassays. The results were compared to those obtained for a commercially available reference compound 2-(thiocyanomethylthio) benzothiazole (TCMTB). Parameters such as surface tension (ϒCMC), critical micelle concentration (CMC), surface excess concentration (Γ), and area per molecule (A) were determined. The resulting values indicated that the five gemini surfactants are characterized by good surface-active and self-aggregation properties. All surfactants were tested to evaluate their antifungal activity. Six fungal strains were used to conduct the study. The minimum inhibitory concentration (MIC) value was measured by the fungal growth inhibition. The results of the MICs were compared with two commercially available reference compounds (Fluconazole and TCMTB). The least active molecule was 3e, but 3b and 3d were found to be the most potent compounds with a similar activity for all strains. Candida albicans was the most sensitive one. In contrast, Aspergillus niger was resistant. Ecotoxicity of gemini 3e was assessed: the commercial formulation (TCMTB) was between three and four orders of magnitude more toxic than the gemini one for the biological species tested.展开更多
Four gemini cationic surfactants {N,N′-di[2-(lauryldimethylamino)acetyl]polymethylenediamine dichloride, LAA-s-LAA, s=2,3,4,6} were synthesized by using four bis(α-chloroacetamide)s and N,N-dimethyllaurylamine, resp...Four gemini cationic surfactants {N,N′-di[2-(lauryldimethylamino)acetyl]polymethylenediamine dichloride, LAA-s-LAA, s=2,3,4,6} were synthesized by using four bis(α-chloroacetamide)s and N,N-dimethyllaurylamine, respectively. The molecular structures were characterized by means of IR, ~ 1H NMR, \{~ ~13 C NMR\} and MS, and the behavior of their aqueous solutions was studied. The critical micell concentrations(CMC) of LAA-s-LAA were one order of magnitude lower than that of dodecyltrimethyl ammonium chloride(DTAC). With the change of the length of spacer chain(s), their CMC values change, and CMC reaches the top value at s=4.展开更多
Five new zwitterionic surfactants with long chain alkyl betaine structure incorporated with hydroxylpropyl group have been synthesized. Their structures were identified by elemental analysis, IR (HNMR)-H-1, and (CNMR)...Five new zwitterionic surfactants with long chain alkyl betaine structure incorporated with hydroxylpropyl group have been synthesized. Their structures were identified by elemental analysis, IR (HNMR)-H-1, and (CNMR)-C-13. Surface tension experiments showed that these surfactants have higher surface activity than those without hydroxypropyl group. The values of CMC and gamma(CMC) of these surfactants have been determined.展开更多
A series of piperazine-based Gemini and Bola surfactants were synthesized. Gemini 1 and 5 have well surface activities. Their critical micelle concentrations （cmc） is 6.47×10^-4 mol/L and 1.17×10^-3mol/L, ...A series of piperazine-based Gemini and Bola surfactants were synthesized. Gemini 1 and 5 have well surface activities. Their critical micelle concentrations （cmc） is 6.47×10^-4 mol/L and 1.17×10^-3mol/L, respectively. Bola surfactants 2 and compound 3, possessing better water solubility, have lower surface activities. Calculation, carried out by MM2 energy minimization, showed that compound with more hydrophobic chains in a spacer of limited length is difficult to be synthesized.展开更多
报道了一种含多酯基不对称阳离子Gem in i表面活性剂(Ⅰ)的合成。在甲醇钠催化下,N,N-二甲基乙醇胺与邻苯二甲酸二甲酯酯交换制得二(N,N-二甲基氨基乙基)邻苯二甲酸酯(Ⅱ),收率92%(以邻苯二甲酸二甲酯计);氯乙酸分别与十二醇、十六醇反...报道了一种含多酯基不对称阳离子Gem in i表面活性剂(Ⅰ)的合成。在甲醇钠催化下,N,N-二甲基乙醇胺与邻苯二甲酸二甲酯酯交换制得二(N,N-二甲基氨基乙基)邻苯二甲酸酯(Ⅱ),收率92%(以邻苯二甲酸二甲酯计);氯乙酸分别与十二醇、十六醇反应合成氯乙酸十二醇酯(Ⅲ)和十六醇酯(Ⅳ),产率分别为93%(以十二醇计)、91%(以十六醇计);(Ⅱ)与(Ⅲ)反应,经石油醚洗涤除去杂质后,再与(Ⅳ)季铵盐化,经乙腈重结晶,得白色晶体(I),采用两相滴定法测定其质量分数为99.5%,收率59%(以氯乙酸十二醇酯计)。用IR1、HNMR、元素分析表征了其结构,测定了其CMC和γCMC,研究了其乳化性和泡沫性质。展开更多
文摘A series of N-acetylated cationic gemini surfactants (3a-e) having dimeric structures derived from tertiary amines were synthesized. Their antifungal potency and surface properties were determined. It also studied the acute toxicity of the molecule with the best performance and the best water solubility (3e) through Chlorella vulgaris and Daphnia magna bioassays. The results were compared to those obtained for a commercially available reference compound 2-(thiocyanomethylthio) benzothiazole (TCMTB). Parameters such as surface tension (ϒCMC), critical micelle concentration (CMC), surface excess concentration (Γ), and area per molecule (A) were determined. The resulting values indicated that the five gemini surfactants are characterized by good surface-active and self-aggregation properties. All surfactants were tested to evaluate their antifungal activity. Six fungal strains were used to conduct the study. The minimum inhibitory concentration (MIC) value was measured by the fungal growth inhibition. The results of the MICs were compared with two commercially available reference compounds (Fluconazole and TCMTB). The least active molecule was 3e, but 3b and 3d were found to be the most potent compounds with a similar activity for all strains. Candida albicans was the most sensitive one. In contrast, Aspergillus niger was resistant. Ecotoxicity of gemini 3e was assessed: the commercial formulation (TCMTB) was between three and four orders of magnitude more toxic than the gemini one for the biological species tested.
文摘Four gemini cationic surfactants {N,N′-di[2-(lauryldimethylamino)acetyl]polymethylenediamine dichloride, LAA-s-LAA, s=2,3,4,6} were synthesized by using four bis(α-chloroacetamide)s and N,N-dimethyllaurylamine, respectively. The molecular structures were characterized by means of IR, ~ 1H NMR, \{~ ~13 C NMR\} and MS, and the behavior of their aqueous solutions was studied. The critical micell concentrations(CMC) of LAA-s-LAA were one order of magnitude lower than that of dodecyltrimethyl ammonium chloride(DTAC). With the change of the length of spacer chain(s), their CMC values change, and CMC reaches the top value at s=4.
文摘Five new zwitterionic surfactants with long chain alkyl betaine structure incorporated with hydroxylpropyl group have been synthesized. Their structures were identified by elemental analysis, IR (HNMR)-H-1, and (CNMR)-C-13. Surface tension experiments showed that these surfactants have higher surface activity than those without hydroxypropyl group. The values of CMC and gamma(CMC) of these surfactants have been determined.
文摘A series of piperazine-based Gemini and Bola surfactants were synthesized. Gemini 1 and 5 have well surface activities. Their critical micelle concentrations （cmc） is 6.47×10^-4 mol/L and 1.17×10^-3mol/L, respectively. Bola surfactants 2 and compound 3, possessing better water solubility, have lower surface activities. Calculation, carried out by MM2 energy minimization, showed that compound with more hydrophobic chains in a spacer of limited length is difficult to be synthesized.
文摘报道了一种含多酯基不对称阳离子Gem in i表面活性剂(Ⅰ)的合成。在甲醇钠催化下,N,N-二甲基乙醇胺与邻苯二甲酸二甲酯酯交换制得二(N,N-二甲基氨基乙基)邻苯二甲酸酯(Ⅱ),收率92%(以邻苯二甲酸二甲酯计);氯乙酸分别与十二醇、十六醇反应合成氯乙酸十二醇酯(Ⅲ)和十六醇酯(Ⅳ),产率分别为93%(以十二醇计)、91%(以十六醇计);(Ⅱ)与(Ⅲ)反应,经石油醚洗涤除去杂质后,再与(Ⅳ)季铵盐化,经乙腈重结晶,得白色晶体(I),采用两相滴定法测定其质量分数为99.5%,收率59%(以氯乙酸十二醇酯计)。用IR1、HNMR、元素分析表征了其结构,测定了其CMC和γCMC,研究了其乳化性和泡沫性质。
