| A series of rosin-based quaternary ammonium with hydroxyl group and rosin-based long alkyl chain ammonium salt were prepared through varied chemical reactions using rosin and its derivatives as raw materials. The structure of products were characterized by IR, 1H NMR and 13 C NMR. The critical micelle concentration(CMC), the surface tensions corresponding to CMC(γCMC), emulsifying properties, foam properties, HLB value and antibacterial activity of rosin-based quaternary ammonium with hydroxyl were studied. Through these performance test, we discussed the influence of different rosin framework, hydroxyl and chain length on rosin-based quaternary ammonium with hydroxyl group. The paper also studied the effects of connection chain length and hydrogen bonding on liquid crystal behavior of synthetic products. These studies can open up a new way for high value utilization of rosin and provide a theoretical guidance for the development of new types of surfactant and liquid crystal materials.Four rosin-based choline quaternary ammonium surfactants were synthesized from dehydroabietic acid, dehydroabietylamine maleic acid, acrylic acid pimaric and maleopimaric. Their CMC value were from 2×10-3 to 8×10-3 mol/L, and γCMC were from 35.1 to 42.4 mN/m. By comparison, we can see the CMC and γCMC values of quaternary ammonium with hydroxyl were less than that of quaternary ammonium without hydroxyl. The result showed that the existence of hydroxyl group can improve the surface activity of quaternary ammonium surfactants. MIC of quaternary ammonium salt Ⅰ1, Ⅰ2, Ⅱ1 and Ⅱ2 against Staphyloccocus epidermidis were 16 mg/L. MIC of Ⅲ1, Ⅲ2, Ⅳ1 and Ⅳ2 against Staphyloccocus epidermidis were 2 mg/L, which were lower than Bromogeramine and Ampicillin Sodium.With rosin and dehydroabietic acid as raw material, three kinds of rosin ester-based quaternary ammonium with hydroxyl were synthesized through acylation, esterification and quaternarization. The CMC values of dehydroabietic acid ester-based quaternary ammonium salt 3a~3h were from 2×10-4 to 9.6×10-4 mol/L, respectively. And the corresponding γCMC were from 27.1 to 34.1 mN/m. Through comparison of compounds having same number of hydroxyl groups, we found that the surface properties were affected by substitution positions. The liquid crystal performance of 3d, 3e and 3f was studied through TG, DSC, POM, FTIR and XRD. The stable glassy state liquid crystal of 3d and 3e were formed in the first cooling and second heating. The glass transition temperature was about 40℃. Hydrogen bonding which were formed by rosin ester quaternary ammonium salt changed at high temperature. The rigid structure of dehydroabietyl and hydrogen bonding interaction made these quaternary ammonium salt difficult to shift from liquid crystal to crystal phase, thus forming a glassy state.A variety kind of rigid alkyl ammonium salts were synthesized through the introduction of long-chain aliohatic amines with the dehydroabietic acid and its derivatives as raw materials. The liquid crystal performance of these compounds was studied through TG, DSC, POM, FTIR and XRD. The result showed that part of rosin-based long alkyl chain ammonium could form liquid crystal phase. With the increase of alkyl chain length, the phase transition temperature of CnDHAAS decreased. With the rise of temperature, hydrogen bonds interaction formed by CnDHAAS and CnDHAMAS gradually weakened. Compared with the structure of CnDHAAS, the linker group between rigid portion and ionic head groups of CnDHAMAS made closer link between long-chain molecules, therefore, the tendency of the phase transition became more difficult. CnDHAAS had glass transition peak during first cooling and second heating process, which showed the performance of liquid crystal glass. |
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