Synthesis and characterization of hydrophobic long-chain fatty acylated cellulose and its self-assembled nanoparticles

Abstract

In this paper, a series of cellulose-based hydrophobic associating polymers were prepared by homogeneous acylation of microcrystalline cellulose with long-chain acyl chlorides including octanoyl, lauroyl, and palmitoly chlorides in the solvent of N,N-dimethylacetamide/lithium chloride (DMAc/LiCl) using pyridine as acid scavenger. Through controlling the chain length of fatty acyl chlorides and the molar ratio of acyl chlorides vs anhydroglucose unit, the hydrophobic cellulose derivatives with degrees of substitution in the range of 0.02-1.75 were successfully obtained. The chemical structures and properties of these hydrophobic derivatives were characterized by elemental analysis, FT-IR, CP/MAS 13 C NMR, X-ray diffraction, and the thermogravimetry analysis. It was also found that, the cellulose-based polymers achieved an excellent solubility in organic solvents, such as benzene, methylbenzene, and pyridine, with the introduction of hydrophobic side chain into the cellulose backbone. Furthermore, it was found that these hydrophobic cellulose derivatives could self-assemble into spherical nanoparticles in aqueous solution, which indicates a tremendous potential of applications in pharmaceutical and medical fields.

An Investigation on the Lubricity Characteristics of Polyethylene Glycol Blends with Cellulose Palmitates

“…The loss of the diffraction peaks of cellulose clearly shows that during the acylation, crystallinity loses due to the loss of hydrogen bonding. These results are similar to the previous reported studies too [24][25][26][27][28].…”

“…Another band at 1649 cm -1 in the cellulose spectrum corresponds to the OH bending due to absorbed water molecules, intensity of which reduces in the ester samples significantly. It also gives an idea of successful acylation which makes the molecules hydrophobic in nature and, consequently, reduces the water molecules absorption tendency [24][25][26][27][28].…”

“…A number of previous studies are reported for cellulose ester synthesis involving various solvent systems with various acylation reagents and catalysts; e.g., Xu et al [24] synthesized the cellulose laureates using cellulose, fatty acid and DMAc/ LiCl using p-toluenesulfonyl chloride (p-TsCl) as activating reagent. Guo et al [25] synthesized a series of cellulose esters using octanoyl, lauroyl, palmitoyl chlorides in the DMAc/LiCl using pyridine as acid scavenger. Tosh et al [26] used DMAc/LiCl solvent system for rayon grade cellulose esterification with acetic anhydride using p-toluenesulfonyl chloride and pyridine as catalyst.…”

A water‐soluble acrylamide hydrophobically associating polymer: Synthesis, characterization, and properties as EOR chemical

“…In a word, PAM is unsuitable given the harsh conditions of high salinity, high temperature, high heterogeneity, and long-time injections which commonly exist in most oil reservoirs due to the hydrolysis, degradation, and others. 13,14 Compared with polyacrylamide, xanthan gum is a rigid polysaccharide that is not readily shear degraded, and is not sensitive to an increase in salinity or divalent ion concentration. 15 Nevertheless, the disadvantages of xanthan also include higher cost, high susceptibility to biodegradation, and potential for injectivity problems due to the cellular debris remaining from the manufacturing process.…”

Derivatização de celulose sob condições homogêneas: cinética e mecanismo de acilação do biopolímero em LiCI/DMAC e liquídos iônicos/solventes apróticos dipolares

“…Derivatization by acyl chloride/tertiary amine is shown in Figure 1.21; base is employed in order to scavenge the liberated HCl, the results are similar to the reaction with acid anhydrides (Guo et al 2012). [61]…”