Study on synthesis, properties, and aggregation behavior of sodium alkyl glycoside sulfate

References

• Dokouhaki, M.; Hung, A.; Kasapis, S.; Gras, S. L. Hydrophobins and Chaplins: Novel Bio-Surfactants for Food Dispersions a Review. Trends Food Sci. Technol. 2021, 111, 378–387. DOI: 10.1016/j.tifs.2021.03.001.
   Web of Science ®Google Scholar
• Varjani, S.; Rakholiya, P.; Yong Ng, H.; Taherzadeh, M. J.; Hao Ngo, H.; Chang, J.-S.; Wong, J. W. C.; You, S.; Teixeira, J. A.; Bui, X.-T. Bio-Based Rhamnolipids Production and Recovery from Waste Streams: Status and Perspectives. Bioresour. Technol. 2021, 319, 124213. DOI: 10.1016/j.biortech.2020.124213.
   PubMed Web of Science ®Google Scholar
• Smułek, W.; Burlaga, N.; Hricovíni, M.; Medveďová, A.; Kaczorek, E.; Hricovíniová, Z. Evaluation of Surface Active and Antimicrobial Properties of Alkyl D-Lyxosides and Alkyl L-Rhamnosides as Green Surfactants. Chemosphere 2021, 271, 129818. DOI: 10.1016/j.chemosphere.2021.129818.
   PubMed Web of Science ®Google Scholar
• Lu, B.; Miao, Y.; Vigneron, P.; Chagnault, V.; Grand, E.; Wadouachi, A.; Postel, D.; Pezron, I.; Egles, C.; Vayssade, M. Measurement of Cytotoxicity and Irritancy Potential of Sugar-Based Surfactants on Skin-Related 3D Models. Toxicol in Vitro 2017, 40, 305–312. DOI: 10.1016/j.tiv.2017.02.002.
   PubMed Web of Science ®Google Scholar
• Zdarta, A.; Pacholak, A.; Smułek, W.; Zgoła-Grześkowiak, A.; Ferlin, N.; Bil, A.; Kovensky, J.; Grand, E.; Kaczorek, E. Biological Impact of Octyl D-Glucopyranoside Based Surfactants. Chemosphere 2019, 217, 567–575. DOI: 10.1016/j.chemosphere.2018.11.025.
   PubMed Web of Science ®Google Scholar
• Fan, Y.; Fu, F.; Chen, L.; Li, J.; Zhang, J. Surface Activity of Alkoxy Ethoxyethyl β-d-Glucopyranosides. J. Agric. Food Chem. 2020, 68, 2684–2695. DOI: 10.1021/acs.jafc.9b05966.
   PubMed Web of Science ®Google Scholar
• Abdellahi, B.; Bois, R.; Golonu, S.; Pourceau, G.; Lesur, D.; Chagnault, V.; Drelich, A.; Pezron, I.; Nesterenko, A.; Wadouachi, A. Synthesis and Interfacial Properties of New 6-Sulfate Sugar-Based Anionic Surfactants. Tetrahedron Lett. 2021, 74, 153113. DOI: 10.1016/j.tetlet.2021.153113.
   Web of Science ®Google Scholar
• Bois, R.; Abdellahi, B.; Mika, B.; Golonu, S.; Vigneron, P.; Chagnault, V.; Drelich, A.; Pourceau, G.; Wadouachi, A.; Vayssade, M.; et al. Physicochemical, Foaming and Biological Properties of Lowly Irritant Anionic Sugar-Based Surfactants. Colloids Surf. A 2020, 607, 125525. DOI: 10.1016/j.colsurfa.2020.125525.
   Google Scholar
• Baez-Santos, Y. M.; Otte, A.; Mun, E. A.; Soh, B. K.; Song, C. G.; Lee, Y. N.; Park, K. Formulation and Characterization of a Liquid Crystalline Hexagonal Mesophase Region of Phosphatidylcholine, Sorbitan Monooleate, and Tocopherol Acetate for Sustained Delivery of Leuprolide Acetate. Int. J. Pharm. 2016, 514, 314–321. DOI: 10.1016/j.ijpharm.2016.06.138.
   PubMedGoogle Scholar
• Liu, J.; Guan, L.; Wang, Z. Phase Behavior of Surfactant Mixtures and the Effect of Alkyl Chain and Temperature on Lyotropic Liquid Crystal. Colloids Surf. A 2020, 585, 124019. DOI: 10.1016/j.colsurfa.2019.124019.
   Google Scholar
• Wang, Z.; Xie, J.; Shen, M.; Nie, S.; Xie, M. Sulfated Modification of Polysaccharides: Synthesis, Characterization and Bioactivities. Trends Food Sci. Technol. 2018, 74, 147–157. DOI: 10.1016/j.tifs.2018.02.010.
   Web of Science ®Google Scholar
• Gonçalves, A. G.; Noseda, M. D.; Duarte, M. E.; R.; Grindley, T. B. Regioselective Synthesis of Long-Chain Ethers and Their Sulfates Derived from Methyl β-d-Galactopyranoside and Derivatives via Dibutylstannylene Acetal Intermediates. Carbohydr. Res. 2005, 340, 2245–2250. DOI: 10.1016/j.carres.2005.07.008.
   PubMed Web of Science ®Google Scholar
• Mukherjee, S.; Ghosh, K.; Hahn, F.; Wangen, C.; Strojan, H.; Müller, R.; Anand, N.; Ali, I.; Bera, K.; Ray, B.; et al. Chemically Sulfated Polysaccharides from Natural Sources: Assessment of Extraction-Sulfation Efficiencies, Structural Features and Antiviral Activities. Int. J. Biol. Macromol. 2019, 136, 521–530. DOI: 10.1016/j.ijbiomac.2019.05.005.
   PubMed Web of Science ®Google Scholar
• Galermo, A. G.; Nandita, E.; Barboza, M.; Amicucci, M. J.; Vo, T.-T. T.; Lebrilla, C. B. Liquid Chromatography–Tandem Mass Spectrometry Approach for Determining Glycosidic Linkages. Anal. Chem. 2018, 90, 13073–13080. DOI: 10.1021/acs.analchem.8b04124.
   PubMed Web of Science ®Google Scholar
• Liu, Q.; Li, J.; Song, X.; Zhang, M.; Li, E.; Gao, F.; He, L. Simultaneous Determination of Aminoglycoside Antibiotics in Feeds Using High Performance Liquid Chromatography with Evaporative Light Scattering Detection. RSC Adv. 2017, 7, 1251–1259. DOI: 10.1039/C6RA26581B.
   Web of Science ®Google Scholar
• Zuo, Y.; Lv, J.; Wei, N.; Chen, X.; Tong, J. Effect of Anions and Cations on the Self-Assembly of Ionic Liquid Surfactants in Aqueous Solution. J. Mol. Liq. 2023, 375, 121342. DOI: 10.1016/j.molliq.2023.121342.
   Web of Science ®Google Scholar
• Jia, X.; Wei, R.; Xu, B.; Liu, H.; Xu, B. C. Green Synthesis, Surface Activity, Micellar Aggregation, and Foam Properties of Amide Quaternary Ammonium Surfactants. ACS Omega 2022, 7, 48240–48249. DOI: 10.1021/acsomega.2c06353.
   PubMed Web of Science ®Google Scholar
• Shaban, S. M.; Fouda, A. S.; Rashwan, S. M.; Ibrahim, H. E.; El-Bhrawy, M. F. Synthesis and Characterization of Newly Cationic Surfactants Based on 2-(2-(Dimethylamino)Ethoxy)Ethanol: Physiochemical, Thermodynamic and Evaluation as Biocide. J. Mol. Liq. 2016, 221, 224–234. DOI: 10.1016/j.molliq.2016.05.088.
   Web of Science ®Google Scholar
• Zhang, T.; Cao, X.; Wang, X.; Song, C. Synthesis, Surface Activity and Thermodynamic Properties of Cationic Gemini Surfactants with Diester and Rigid Spacers. J. Mol. Liq. 2017, 230, 505–510. DOI: 10.1016/j.molliq.2017.01.063.
   Web of Science ®Google Scholar
• Ren, C.; Wang, F.; Zhang, Z.; Nie, H.; Li, N.; Cui, M. Synthesis, Surface Activity and Aggregation Behavior of Gemini Imidazolium Surfactants 1,3-Bis(3-Alkylimidazolium-1-yl) Propane Bromide. Colloids Surf. A 2015, 467, 1–8. DOI: 10.1016/j.colsurfa.2014.11.031.
   Web of Science ®Google Scholar
• Zhu, Q.; Pan, F.; Tian, Y.; Tang, W.; Yuan, Y.; Hu, A. Facile Synthesis of Gd(Iii) Metallosurfactant-Functionalized Carbon Nanodots with High Relaxivity as Bimodal Imaging Probes. RSC Adv. 2016, 6, 29441–29447. DOI: 10.1039/C6RA02654K.
   Web of Science ®Google Scholar
• Li, J.; Zhang, J.; Chen, L.; Zhang, G.; Liao, J. Surface Properties and Liquid Crystal Properties of Alkyltetra(Oxyethyl) Beta-d-Glucopyranoside. J. Agric Food. Chem. 2021, 69, 10617–10629. DOI: 10.1021/acs.jafc.1c03630.
   PubMed Web of Science ®Google Scholar
• Majeed, T.; Sølling, T. I.; Kamal, M. S. Foamstability: The Interplay between Salt-, Surfactant- and Critical Micelle Concentration. J. Pet. Sci. Eng. 2020, 187, 106871. DOI: 10.1016/j.petrol.2019.106871.
   Web of Science ®Google Scholar
• Qiao, L.; Zhang, W.; Xu, L.; Han, F.; Zhou, Y.; Xu, B. Synthesis and Properties of PH‐Dependent Gemini Surfactants Containing Multiple Carboxyl Groups. J. Surfactants Deterg. 2020, 23, 263–271. DOI: 10.1002/jsde.12390.
   Web of Science ®Google Scholar
• Paye, C. M.; Hamaide, N.; Hüttmann, G.-E.; Kirkwood, S.; Lally, C.; Lloyd, P. H.; Makela, P.; Razenberg, H.; Young, R. Antagonisms between Surfactants: The Case of Laundry Detergents. Tenside Surf. Det. 2006, 43, 6. DOI: 10.3139/113.100316.
   Web of Science ®Google Scholar
• Li, C.; Feng, C.; Tian, M.; Meng, X.; Zhao, C. A Novel Approach for Echinacoside and Acteoside Extraction from Cistanche Deserticola Y. C. Ma Using an Aqueous System Containing Ionic Liquid Surfactants. Sustainable Chem. Pharm. 2022, 26, 100644. DOI: 10.1016/j.scp.2022.100644.
   Web of Science ®Google Scholar
• Qian, X. P.; Zha, X. Q.; Xiao, J. J.; Zhang, H. L.; Pan, L. H.; Luo, J. P. Sulfated Modification Can Enhance Antiglycation Abilities of Polysaccharides from Dendrobium Huoshanense. Carbohydr. Polym. 2014, 101, 982–989. DOI: 10.1016/j.carbpol.2013.10.035.
   PubMed Web of Science ®Google Scholar
• Zhu, M.; Wang, C.; Wang, X.; Chen, S.; Zhu, H.; Zhu, H. Extraction of Polysaccharides from Morinda Officinalis by Response Surface Methodology and Effect of the Polysaccharides on Bone-Related Genes. Carbohydr. Polym. 2011, 85, 23–28. DOI: 10.1016/j.carbpol.2011.01.016.
   Web of Science ®Google Scholar
• Li, Z.; Wu, H.; Hu, Y.; Chen, X.; Yuan, Y.; Luo, Y.; Hou, J.; Bai, B.; Kang, W. Ultra-Low Interfacial Tension Biobased and Catanionic Surfactants for Low Permeability Reservoirs. J. Mol. Liq. 2020, 309, 113099. DOI: 10.1016/j.molliq.2020.113099.
   Web of Science ®Google Scholar
• Zhou, M.; Zhang, Z.; Xu, D.; Hou, L.; Zhao, W.; Nie, X.; Zhou, L.; Zhao, J. Synthesis of Three Gemini Betaine Surfactants and Their Surface Active Properties. J. Taiwan Inst. Chem. Eng. 2017, 74, 7–13. DOI: 10.1016/j.jtice.2016.10.012.
   Web of Science ®Google Scholar
• Li, P.; Guo, Y.; Lu, Z.; Zhang, W.; Hou, L. Syntheses, Surface Activities and Aggregation Morphologies of a Series of Novel Itaconic Acid Based Asymmetrical Gemini Surfactants. J. Mol. Liq. 2019, 290, 111218. DOI: 10.1016/j.molliq.2019.111218.
   Web of Science ®Google Scholar
• Zhong, X.; Guo, J. W.; Feng, L. J.; Xu, X. J.; Zhu, D. Y. Cationic Gemini Surfactants Based on Adamantane: Synthesis, Surface Activity and Aggregation Properties. Colloids Surf. A 2014, 441, 572–580. DOI: 10.1016/j.colsurfa.2013.10.016.
   Google Scholar
• Song, Y.; Li, Q.; Li, Y.; Zhi, L. Surface and Aggregation Properties of Heterogemini Surfactants Containing Quaternary Ammonium and Guanidine Moiety. Colloids Surf. A 2013, 417, 236–242. DOI: 10.1016/j.colsurfa.2012.11.004.
   Google Scholar
• Chang, H.; Wang, Y.; Cui, Y.; Li, G.; Zhang, B.; Zhao, X.; Wei, W. Equilibrium and Dynamic Surface Tension Properties of Gemini Quaternary Ammonium Salt Surfactants with Hydroxyl. Colloids Surf. A 2016, 500, 230–238. DOI: 10.1016/j.colsurfa.2016.04.029.
   Google Scholar
• Chai, J. L.; Cui, X. C.; Zhang, X. Y.; Song, M. M.; Wang, J.; Lu, J. J. Adsorption Equilibrium and Dynamic Surface Tension of Alkyl Polyglucosides and Their Mixed Surfactant Systems with CTAB and SDS in the Surface of Aqueous Solutions. J. Mol. Liq. 2018, 264, 442–450. DOI: 10.1016/j.molliq.2018.05.055.
   Web of Science ®Google Scholar
• Zhang, H.; Wang, J. Q.; Nie, S. P.; Wang, Y. X.; Cui, S. W.; Xie, M. Y. Sulfated Modification, Characterization and Property of a Water-Insoluble Polysaccharide from Ganoderma Atrum. Int. J. Biol. Macromol. 2015, 79, 248–255. DOI: 10.1016/j.ijbiomac.2015.04.070.
   PubMed Web of Science ®Google Scholar
• Wang, L.; Li, X.; Chen, Z. Sulfated Modification of the Polysaccharides Obtained from Defatted Rice Bran and Their Antitumor Activities. Int. J. Biol. Macromol. 2009, 44, 211–214. DOI: 10.1016/j.ijbiomac.2008.12.006.
   PubMed Web of Science ®Google Scholar
• Garcia, M. T.; Kaczerewska, O.; Ribosa, I.; Brycki, B.; Materna, P.; Drgas, M. Hydrophilicity and Flexibility of the Spacer as Critical Parameters on the Aggregation Behavior of Long Alkyl Chain Cationic Gemini Surfactants in Aqueous Solution. J. Mol. Liq. 2017, 230, 453–460. DOI: 10.1016/j.molliq.2017.01.053.
   Web of Science ®Google Scholar
• Larsson, J.; Sanchez-Fernandez, A.; Mahmoudi, N.; Barnsley, L. C.; Wahlgren, M.; Nylander, T.; Ulvenlund, S. Effect of the Anomeric Configuration on the Micellization of Hexadecylmaltoside Surfactants. Langmuir 2019, 35, 13904–13914. DOI: 10.1021/acs.langmuir.9b01960.
   PubMed Web of Science ®Google Scholar
• Ou, J.; Kong, Z.; Yang, R.; Dai, Z. Synthesis of a Lignin-Based Alcohol Ether Carboxylate Surfactant and Its Application as Cotton Fiber Detergent. J. Dispers. Sci. Technol. 2023, 44, 577–584. DOI: 10.1080/01932691.2021.1956323.
   Web of Science ®Google Scholar
• Cohen, L.; Sanchez, E.; Martin, M.; Soto, F.; Trujillo, F. Study of the Effects of LAS and Zein Concentrations on Protein Solubilization. J. Surfact. Deterg. 2016, 19, 1089–1092. DOI: 10.1007/s11743-016-1846-3.
   Web of Science ®Google Scholar
• Böcker, T.; Lindhorst, T. K.; Thiem, J.; Vill, V. Synthesis and Properties of Sulfated Alkyl Glycosides. Carbohydr. Res. 1992, 230, 245–256. DOI: 10.1016/0008-6215(92)84036-R.
   PubMed Web of Science ®Google Scholar