Phenoxyhydroxypropylhydroxyethylcellulose—new amphiphilic cellulose derivative

Danilevicius, A.; Dobilienė, Justina; Wutz, Christoph; Liesienė, Jolanta

doi:10.1007/s10570-006-9105-9

Cited by 7 publications

(6 citation statements)

References 13 publications

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“…The typical examples include cationic cellulose [5,6], acylated cellulose [7,8], etherificated cellulose [9][10][11][12], hydrophobic cellulose [13][14][15][16][17] as well as amphiphilic cellulose [18][19][20][21][22]. Owing to their non-toxicity, biotolerability, biodegradability, and chemical stability, these cellulose-based polymers can be used as functional biomaterials, bioplastics, and bioenergy to reduce global dependence on the fossil resources.…”

Section: Introductionmentioning

confidence: 99%

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

Guo

Wang

et al. 2012

Polym. Bull.

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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.

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Section: Introductionmentioning

confidence: 99%

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

Guo

Wang

et al. 2012

Polym. Bull.

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“…Landoll [6] was the first to develop amphiphilic cellulose derivatives, and these were synthesized through the reaction of nonionic cellulose ethers with long-chain nalkyl epoxides. Following his research, much of the work in this area focused on the synthesis of cellulose derivatives bearing various hydrophobic residues, such as alkyl groups, bulky phenoxyhydroxypropyl groups, poly(ε-caprolactone) segments, and poly(methyl methacrylate) segments [7][8][9][10]. Bulky cholesteryl-modified amphiphilic chitosan [11][12][13], carboxymethylcellulose [14,15], and sodium alginate [16] derivatives were reported to represent a new kind of biomaterial.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel liquid crystalline cholesteryl-modified hydroxypropyl cellulose derivatives

Bagheri

Shateri

2012

J Polym Res

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Two new series of cholesteryl-modified hydroxypropyl cellulose (HPC) derivatives were synthesized by performing reactions involving HPC, a cholesterol-based mesogenic dimer (HPC-G1-Chol), or cholesteryl chloroformate (HPC-Chol), all with different degrees of substitution (D Chol ). All of the compounds obtained were characterized by conventional spectroscopic methods. The D Chol values of the modified HPCs was obtained using 1 H NMR spectroscopy. Thermogravimetric analysis and differential scanning calorimetry (DSC) in combination with polarizing optical microscopy (POM) were used to investigate the thermal properties of the compounds obtained. The glass transitions of the modified HPCs occurred at lower temperatures than the glass transition temperature for HPC, but the glass transition temperatures increased with increasing D Chol . All of the synthesized polymers formed thermotropic liquid crystalline phases. Polymers with a mesogenic side chain (i.e., the HPC-G1-Chol series) had wider mesophases than HPC and polymers that were derived from HPCChol. These compounds were found to be soluble in a variety of organic solvents, so they formed lyotropic liquid crystal mesophases in acetone. The critical concentrations above which liquid crystalline order was observed were 20 and 25 wt% for a sample from each series (HPC-G1-Chol and HPC-Chol, respectively) in acetone. It can therefore be hypothesized that HPC-G1-Chol has a greater propensity to exhibit specific chain-chain association phenomena than HPC-Chol in acetone.

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“…Landoll (Landoll 1982) was the first to develop the amphiphilic cellulose derivatives, which were synthesized through the reaction of nonionic cellulose ethers like hydroxyethyl cellulose (HEC), hydroxypropyl cellulose (HPC) and methylcellulose (MC) with long-chain n-alkyl epoxides. Following his research, a large proportion of the work focused on synthesis of cellulose derivatives bearing various hydrophobic residues, such as alkyl groups (Nishimura et al 1997;Srokova et al 2004;Ye and Huang 2006;Wei and Cheng 2007), bulky phenoxyhydroxypropyl groups (Danilevicius et al 2007), poly (e-caprolactone) segments (Shi and Burt 2003;Yuan et al 2007) and poly(methyl methacrylate) segments (Ostmark et al 2007).…”

Section: Introductionmentioning

confidence: 99%

Amphiphilic cholesteryl-bearing carboxymethylcellulose derivatives: self-assembly and rheological behaviour in aqueous solution

Yang

Kuang

et al. 2008

Cellulose

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The self-assembly of amphiphilic cholesteryl-bearing carboxymethylcellulose derivatives (CCMCs) from individual molecules to self-aggregates, in addition to their rheological behaviour in aqueous solution were investigated. The conformations of the individual CCMC individual molecules and self-aggregates, and the microstructures of CCMC self-aggregates were characterized using the static and dynamic light scattering analyses, and the steady fluorescence technology. The results showed that the individual CCMC chains became compact, and aqueous NaCl solution changed from an approximate h solvent to a bad one when the number of hydrophobic cholesteryl groups increased. The CCMC self-aggregates exhibited as compact spheres. The microstructural characterization indicated that one CCMC self-aggregate consisted of multiple individual CCMC molecules and hydrophobic microdomains, and multiple cholesteryl groups selfassociated into one hydrophobic microdomain. The atomic force microscopy images of CCMC selfaggregates in phase mode showed that the multiple interior hydrophobic phase separation regions were surrounded by hydrophilic polysaccharide chains, providing an evidence for multiple hydrophobic microdomains in one self-aggregate. The rheological analysis proved that the CCMC self-aggregates were a microgel, in which the associations of cholesteryl groups provided multiple cross-linking points in the polymer network. The microgel solutions displayed a unique thixotropy and a shear thinning behaviour.

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Phenoxyhydroxypropylhydroxyethylcellulose—new amphiphilic cellulose derivative

Cited by 7 publications

References 13 publications

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

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

Synthesis and characterization of novel liquid crystalline cholesteryl-modified hydroxypropyl cellulose derivatives

Amphiphilic cholesteryl-bearing carboxymethylcellulose derivatives: self-assembly and rheological behaviour in aqueous solution

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