Surface Properties and Liquid Crystal Properties of Alkyltetra(oxyethyl) β-d-Glucopyranoside

Hydrophilic alkyl polyglycosides (APGs) and alkyl glycosides (AGs) with anomeric pure are a class of important substitutes for petroleum-based surfactants. Improving their water solubility should make such hydrophilic glycosurfactants have more excellent potential application value. To solve the inherent problem of poor water solubility of traditional alkyl β-d-glucopyranoside (5), a series of alkyltetra(oxyethyl) β-d-glucopyranosides (4a–4g, n = 7–18) were successfully synthesized by introducing tetra(oxyethylene) fragments to carry out the structural modification. The relationship between the related structure and the physicochemical properties was further investigated, including their hydrophilic–lipophilic balance (HLB), water-solubility, foaming performance, emulsification, hygroscopicity, surface activity, and thermotropic/lyotropic liquid crystal phase behavior. The results showed that the water solubility gradually decreased as the alkyl chain length increased due to the gradual decrease of their HLB number. Octadecyltetra(oxyethyl) β-d-glucopyranoside (4g, n = 18) was found to be insoluble in water at 25 °C. Taken together, long-chain alkyl glycosides had good foaming properties and excellent emulsifying properties. Among them, dodecyltetra(oxyethyl) β-d-glucopyranoside (4d, n = 12) had the best foaming performance. In the rapeseed oil/water system, cetyltetra(oxyethyl) β-d-glucopyranoside (4f, n = 16) had the best emulsifying ability. With the increase of the alkyl chain length, the critical micelle concentration (Ccmc), γcmc, Γmax, and hygroscopicity of this series of glycosides showed a downward trend. Differential scanning calorimetry (DSC) and polarizing optical microscopy (POM) showed that the thermal stability increased with the increase of the alkyl chain length, and alkyltetra(oxyethyl) β-d-glucopyranosides (4d–4g, n = 12–18) had the corresponding melting points and clearing points. Alkyltetra(oxyethyl) β-d-glucopyranosides (4b–4g, n = 8–18) formed a smectic phase with a typical fan-shaped and focal conic texture during the cooling process. In the water contact experiments, it was found that glycosides (4b–4g, n = 8–18) at high concentrations transformed into various lyotropic liquid crystal including hexagonal phase, bicontinuous cubic phase, and lamellar phase phases. Therefore, such green nonionic glycosurfactants alkyltetra(oxyethyl) β-d-glucopyranosides should have potential practical application prospects.