Preparation And Properties Of Comb-like Ionic Polymeric Surfactants Based On Rosin And Chitosan

Polymeric surfactants are the macromolecular compound with surface activities and theirmolecular weight is over from several thousand to tens of thousands. They have attracted moreand more attentions because they have the properties of both macromolecular compound andsurfactant.CHPDMDHA and ADMDHA were synthesized for the first time withdehydroabietylamine as basic material. The quaterary modifications of LWCTSs, N-CMC,N,O-CMC, N-CEC and N,O-CEC with CHPDMDHA and ADMDHA as active quaternaryammonium salt were put forward innovatively. Four series of rosin modified chitosancomb-like polymeric surfactants involving CHPDMDHA-g-LWCTSs,CHPDMDHA-g-CACTSs, ADMDHA-g-LWCTSs and ADMDHA-g-CACTSs were obtainedrespectively. The products were characterized by FT-IR, NMR and elemental analysis.Meanwhile, the surface activity, emulsifying ability, antibacterial activities and antitumoractivities in vitro were also investigated for the synthesized compound. The relationshipsbetween the performance and the structure were discussed preliminarily. It is expected that theresearch results could play a guiding role for the development of polymeric ionic surfactantsbased on rosin and chitosan.The surface activities of CHPDMDHA, ADMDHA and rosin modified chitosan comb-likepolymeric surfactant were estimated by hanging plate method. The results showed thatCHPDMDHA, ADMDHA and rosin modified chitosan comb-like polymeric surfactant alldisplayed good surface activities. The surface activities of CHPDMDHA is better than that ofthe C12~C16alkyl dimethyl benzyl ammonium chloride which has the similar structure withCHPDMDHA. The surface activity of ADMDHA is also better than that of the C16or C18alkyl dimethyl allyl ammonium chloride which has the similar structure with ADMDHA.Thecritical micelle concentration (cmc) of rosin modified chitosan comb-like polymeric surfactants obtained in our investigation were varied from0.75×10-4mol/L to7.31×10-2mol/L, andincreased with the increase of molecular weight (Mw) of LWCTS and decreased with theincrease of quaternary degree (DQ). Their surface tensions at cmc (γcmc) in aqueous solutionwere varied from31.4mN/m to39.4mN/m and decreased with the increase of the Mw ofLWCTS or the DQ.The influences of CHPDMDHA, ADMDHA, and rosin modified chitosan comb-likepolymeric surfactant on the emulsion stability based on paraffin-water system wereinvestigated respectively. The results showed that the emulsifying ability of CHPDMDHA isbetter than that of the C12~C16alkyl dimethyl benzyl ammonium chloride and the emulsifyingability of ADMDHA is also better than that of the C16or C18alkyl dimethyl allyl ammoniumchloride. The emulsification time of CHPDMDHA-g-LWCTSs, CHPDMDHA-g-CACTSs,ADMDHA-g-LWCTSs and ADMDHA-g-CACTSs were extended with the increase of the DQor Mw of LWCTS.The minimum inhibition concentrations (MICs) of CHPDMDHA, ADMDHA, CA-CTS,CHPDMDHA-g-LWCTSs, CHPDMDHA-g-CACTSs, ADMDHA-g-LWCTSs andADMDHA-g-CACTSs against Pseudomonas aeruginosa, Escherichia aerogenes, Klebsiellapneumonia, Escherichia coil, Staphylococcus aureus, and Staphylococcus epidermidis wereestimated by the2-fold agar dilution method. The relationship between the product’santibacterial activities and their structure were investigated preliminarily. The results showedthat CHPDMDHA and ADMDHA could exhibit obvious inhibitory effects on Staphylococcusaureus and Staphylococcus epidermidis, their MICs were16, and64,8and8μg/mL,respectively. The CA-CTSs could behaviour a good antibacterial activity against Escherichiacoil, Staphylococcus epidermidis, and Pseudomonas aeruginosa and their antibacterialactivities against these bateria declined declined with the increase of their degree ofsubstitution (DS) or the molecule weight. The CHPDMDHA-g-LWCTSs could exhibit moreobvious inhibitory effects against Pseudomonas aeruginosa, their MICs tended to decrease atbegin and then increase with the increasing of DQ and to increase with the increase of Mw of LWCTS. The MICs of CHPDMDHA-g-CACTSs against Escherichia coil tended to decrease atbegin and then increase with the increasing of DQ or Mw of LWCTSs contained in thehydrophilic group. The ADMDHA-g-LWCTSs could behave more obvious inhibitory effectsagainst Pseudomonas aeruginosa, Escherichia aerogenes, and Escherichia coil, their MICsdecreased at begin and then increased with the increase of Mw of LWCTSs, and decreased withthe increasing of the DQ. The ADMDHA-g-N-CMC and ADMDHA-g-N-CEC could exhibit agood inhibitory effect against Escherichia aerogenes, Klebsiella pneumonia, Escherichia coil,and Staphylococcus aureus, their antibacterial activities strengthened with the increasing of DQand tended to increase at begin and then decrease with the increase of Mw of LWCTS.The half inhibitory concentration (IC50) of CHPDMDHA, ADMDHA, CA-CTS,CHPDMDHA-g-LWCTSs, CHPDMDHA-g-CACTSs, ADMDHA-g-LWCTSs andADMDHA-g-CACTSs against human lung cancer H460cells, breast cancer MCF7cells,hepatoma SMMC7721cells and gastric cancer MKN45cells were estimated by MTT method.The research results showed that CHPDMDHA-g-CACTSs3000displayed extensive antitumoractivities against the tested tumor cells. The IC50of CHPDMDHA-g-N-CMC3000againstgastric cancer MKN45cells, CHPDMDHA-g-N,O-CMC3000against hepatoma SMMC7721cells, and CHPDMDHA-g-N,O-CEC3000against hepatoma SMMC7721cells and gastriccancer MKN45cells were all lower than100μg/mL. The ADMDHA-g-N-CEC3000couldbehave some antimuor activities against breast cancer MCF7cells, hepatoma SMMC7721cellsand gastric cancer MKN45cells and its IC50against these cancer cells were75.99,62.69, and99.93μg/mL, respectively. The IC50of ADMDHA against lung cancer H460cells, breastcancer MCF7cells, hepatoma SMMC7721cells and gastric cancer MKN45cells were7.10,10.00,4.91and5.63μg/mL, respectively; the IC50of CHPDMDHA against gastric cancerMKN45cells was9.45μg/mL, these data indicated they could display better antitumoractivities in vitro against these tested tumor cells.