Skip to main content
Log in

Phenoxyhydroxypropylhydroxyethylcellulose—new amphiphilic cellulose derivative

  • Original paper
  • Published:
Cellulose Aims and scope Submit manuscript

Abstract

A new amphiphilic cellulose derivative phenoxyhydroxypropylhydroxyethylcellulose of substitution degree up to 0.67 was synthesized by reaction of water-soluble hydroxyethylcellulose with 2,3-epoxypropylphenylether in the presence of sodium hydroxide as a catalyst. The chemical composition of the derivative was confirmed by means of UV, IR- and 13C-NMR-spectroscopy. The derivatives with substitution degree up to 0.12 are soluble in water and water–alcohol mixtures. With increasing substitution degree, the polymers lose their water solubility, but still dissolve in water–alcohol mixtures. All products are soluble in aprotic solvents. The effect of the reaction conditions, such as temperature and molar ratios of reaction components, on both the reaction rate and degree of substitution was investigated.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

Abbreviations

DS:

Substitution degree

EPPE:

2,3-Epoxypropylphenylether

HEC:

Hydroxyethylcellulose

IPA:

Isopropyl alcohol

LD:

Ligand density

PHPHEC:

Phenoxyhydroxypropylhydroxyethylcellulose

References

  • Edgar KJ, Buchanan CM, Debenham JS, Rundquist PA, Seiler BD, Shelton MC, Tindall D (2001) Advances in cellulose ester performance and application. Prog Polym Sci 26:1605–1688

    Article  CAS  Google Scholar 

  • Heinze T, Liebert T (2001) Unconventional methods in cellulose functionalization. Prog Polym Sci 26:1689–1762

    Article  CAS  Google Scholar 

  • Hoy KL, Hoy RC (1984) US Pat. 4, 228, 277

  • Klemm D, Philipp B, Heinze T, Heinze U (1998) Comprehensive cellulose chemistry, vol. 2. Wiley-VCH, Weinheim, New-York, Chichester, Brisbane, Singapore, Toronto

    Google Scholar 

  • Kroon G (1993) Associative behaviour of hydrophobically-modified hydroxyethylcelluloses (HMHECS) in waterborne coatings. Prog Org Coat 22:245–260

    Article  CAS  Google Scholar 

  • Landoll LM (1980). US Pat. 4, 426, 485

  • Lopez-Velazquez D, Bello A, Perez E (2004) Preparation and characterization of hydrophobically modified hydroxypropylcellulose: side-chain crystallization. Macromol Chem Phys 205:1886–1892

    Article  CAS  Google Scholar 

  • Pillai O, Panchagnula R (2001) Polymers in drug delivery. Curr Opin Chem Biol 5:447–451

    Article  CAS  Google Scholar 

  • Srokova I, Minikova S, Ebringerova A, Sasinkova V, Heinze T (2003) Tenside Surfact. Det 40:73–76

    CAS  Google Scholar 

  • Srokova I, Tomanova V, Ebringerova A, Malovikova A, Heinze T (2004) Water-soluble amphiphilic O-(carboxymethyl)cellulose derivatives—synthesis and properties. Macromol Mat Eng 289:63–69

    Article  CAS  Google Scholar 

  • Stuart MAC, Fokkink RG, van der Horst PM, Lichtenbelt JWT (1998) The adsorption of hydrophobically modified carboxymethylcellulose on a hydrophobic solid: effects of pH and ionic strength. Colloid Polym Sci 276:335–341

    Article  Google Scholar 

  • Tanaka R, Meadows J, Williams PA, Phillips GO (1992) Interaction of hydrophobically modified (hydroxyethyl)cellulose with various added surfactants. Macromolecules 25:1304–1310

    Article  CAS  Google Scholar 

  • Tezuka Y, Imai K, Oshima M, Chiba T (1989) Determination of substituent distribution in cellulose ethers by means of a 13C nuclear magnetic resonance study on their acetylated derivatives: 3. Hydroxyethylcellulose. Polymer 30:2288–2291

    Article  CAS  Google Scholar 

  • Zadorecki P, Hjertberg T, Ardwidsson M (1987) Characterization of cellulose ethers by 13C NMR, 2. Structural determination. Makromol Chem 188:513–525

    Article  CAS  Google Scholar 

  • Zhang LM (2001a) New water-soluble cellulosic polymers: a review. Macromol Mater Eng 286:267–275

    Article  CAS  Google Scholar 

  • Zhang LM (2001b) Cellulosic associative thickeners. Carbohydr Polym 45:1–10

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jolanta Liesiene.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Danilevicius, A., Dobiliene, J., Wutz, C. et al. Phenoxyhydroxypropylhydroxyethylcellulose—new amphiphilic cellulose derivative. Cellulose 14, 321–329 (2007). https://doi.org/10.1007/s10570-006-9105-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10570-006-9105-9

Keywords

Navigation