Dehydroabietyl Glycidyl Ether Grafted Hydroxyethyl Chitosan: Synthesis, Characterization and Physicochemical Properties

Ting Wang; Zhao-sheng Cai; Ting-ting Zhang; Man Li; Gui-gan Fang; Xue-mei Zhu

doi:10.3139/113.110618

Artikel

Dehydroabietyl Glycidyl Ether Grafted Hydroxyethyl Chitosan: Synthesis, Characterization and Physicochemical Properties

Ting Wang , Zhao-sheng Cai , Ting-ting Zhang , Man Li , Gui-gan Fang und Xue-mei Zhu

Veröffentlicht/Copyright: 6. Mai 2019

Veröffentlicht von

Veröffentlichen auch Sie bei De Gruyter Brill

Informationen für Autor*innen

Aus der Zeitschrift Tenside Surfactants Detergents Band 56 Heft 3

Abstract

A series of novel polymeric nonionic surfactants based on water-soluble N,O-hydroxyethyl chitosan (N,O-HECTS) and dehydroabietyl glycidyl ether (DAGE), DAGE-g-N,O-HECTSs, were synthesized by an additive reaction between N,O-HECTS and DAGE. The structures of DAGE-g-N,O-HECTSs were characterized by FT-IR and ¹H NMR. The substitution degree of hydroxyethylation (DS_HE) of N,O-HECTS and the grafting degree (DG) of DAGE onto N,O-HECTS for DAGE-g-N,O-HECTSs were determined by elemental analysis. The surface activities of DAGE-g-N,O-HECTSs in aqueous solution were investigated by measuring the surface tension. The experimental results showed that the degree of grafting (DG) of DAGE-gN,O-HECTSs could have a significant impact on their critical micelle concentrations (CMCs) and surface tensions at the CMC (γ_CMC), but the DG of DAGE-g-N,O-HECTSs had almost no effect on the minimum of surface tensions (γ_min). When using the DAGE-g-N,O-HECTSs as emulsifier, the increase in DG had a favorable influence on the stability of an emulsion of water and benzene. At a DG greater than 40.45%, the emulsifying power of DAGE-g-N,O-HECTS exceeded that of Tween-60.

Kurzfassung

Eine Reihe neuer nichtionischer Polymertenside (DAGE-g-N,O-HECTSs) auf der Basis von wasserlöslichem N,O-Hydroxyethylchitosan (N,O-HECTS) und Dehydroabietylglycidylether (DAGE) wurde durch Additionsreaktion zwischen N,O-HECTS und DAGE synthetisiert. Die Strukturen der DAGE-g-N,O-HECTSs wurden mittels FT-IR und ¹H-NMR charakterisiert. Der Substitutionsgrad der Hydroxyethylierung (DSHE) von N,O-HECTS und der Pfropfgrad (DG) von DAGE auf N,O-HECTS für die DAGE-g-N,O-HECTSs wurden durch Elementaranalyse bestimmt. Die Oberflächenaktivitäten der DAGE-g-N,O-HECTSs in wässriger Lösung wurden durch Messung der Oberflächenspannung untersucht. Die experimentellen Ergebnisse zeigten, dass der Pfropfgrad DG von DAGE-g-N,O-HECTSs einen signifikanten Einfluss auf ihre kritischen Mizellenbildungskonzentrationen (CMCs) und auf die Oberflächenspannungen bei der CMC (γ_CMC) haben könnte, aber der DG von DAGE-g-N,O-HECTSs hatte nahezu keine Auswirkung auf das Minimum der Oberflächenspannungen (γ_min). Bei der Verwendung der DAGE-g-N,O-HECTSs als Emulgatoren hatte die Erhöhung des DG einen günstigen Einfluss auf die Stabilität einer Emulsion aus Wasser und Benzen. Bei einem DG größer als 40,45% konnte die Emulgierkraft von DAGE-g-N,O-HECTS die von Tween-60 übertreffen.

Key words: Polymeric nonionic surfactants; N,O-hydroxyethyl chitosan; Surface activities; Emulsifying property

Stichwörter: Nichtionische Polymertenside; N,O-Hydroxyethylchitosan; Oberflächenaktivitäten; emulgierende Eigenschaften

∗Correspondence address, Prof. Dr. Zhao-sheng Cai, School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng 224051, Jiangsu Province, P.R. China, Tel.: +8651588298429, Fax: +8651588298190, E-Mail: jsyc_czs@163.com

Ting Wang is a bachelor of the Yancheng Institute of Technology. Her main study area is the synthesis and application of fine chemicals based on rosin and other biomass resource.

Zhao-sheng Cai is a professor at the Yancheng Institute of Technology. He graduated from the Institute of Chemical Industry of Forest Products in 2009 and received a Ph.D. degree. His main study area is the synthesis and analysis of fine chemicals, the development and utilization of biomass resource and surfactant, chemical modification of natural materials.

Ting-ting Zhang is bachelor of the Yancheng Institute of Technology. Her main study area is the utilization of biomass resource and interface chemistry.

Man Li is a master of the Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry. Her main study area is the synthesis and application of fine chemicals based on rosin and other biomass resource.

Gui-gan Fang is a professor at the Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry. He graduated from the Chinese Academy of Forestry in 2000 and received a Ph.D. degree. He works in the Institute of Chemical Industry of Forest Products and engages in research on the preparation and development of biomass-based functional polymer materials and new biomass-based chemicals.

Xue-mei Zhu is an associate professor at the Yancheng Institute of Technology. Her main study area is the utilization of biomass resource and interface chemistry.

References

1. Huo, M., Zou, A., Yao, C., Zhang, Y., Zhou, J., Wang, J., Zhu, Q., Li, J. and Zhang, Q.: Somatostatin receptor-mediated tumor-targeting drug delivery using octreotide-PEG-deoxycholic acid conjugate-modified N-deoxycholic acid-O,N-hydroxyethylation chitosan micelles; Biomaterials, 33 (2012) 6393–6407. 10.1016/j.biomaterials.2012.05.052Suche in Google Scholar PubMed

2. Rinaudo, M.: Chitin and chitosan: Properties and applications; Prog. Polym. Sci., 31 (2006) 603–632. 10.1016/j.progpolymsci.2006.06.001Suche in Google Scholar

3. Dash, M., Chiellini, F., Ottenbrite, R. M. and Chiellini, E.: Chitosan-A versatile semi-synthetic polymer in biomedical applications; Prog. Polym. Sci., 36 (2011) 981–1014. 10.1016/j.progpolymsci.2011.02.001Suche in Google Scholar

4. Kumar, R., Muzzarelli, M. N. V., Muzzarelli, R. A. A., Sashiwa, C. H. and Domb, A. J.: Chitosan chemistry and pharmaceutical perspectives; Chem. Rev., 104 (2004) 6017–6084. 10.1021/cr030441bSuche in Google Scholar PubMed

5. Nguyen, M. K. and Alsberg, E.: Bioactive factor delivery strategies from engineered polymerhydrogels for therapeutic medicine; Prog. Polym. Sci.39 (2014) 1235–1265. 10.1016/j.progpolymsci.2013.12.001Suche in Google Scholar PubMed PubMed Central

6. Liu, J., Huang, Y., Kumar, A., Tan, A., Jin, S., Mozhi, A. and Liang, X-J.: pH-Sensitive nano-systems for drug delivery in cancer therapy; Biotechnol. Adv., 32 (2014) 693–710. 10.1016/j.biotechadv.2013.11.009Suche in Google Scholar PubMed

7. Vitková, Z., Oremusová, J., Herdová, P., Vitko, A. and Ivanková, O.: Model Based Approach to Study of Release Kinetics of the Drug Chlorhexidine from Hydrogels; Tenside Surf. Det.52 (2015) 67–72. 10.3139/113.110350Suche in Google Scholar

8. Zhao, C., Nie, S., Tang, M. and SunS.: Polymeric pH-sensitive membranes – A review; Prog. Polym. Sci., 36 (2011) 1499–1520. 10.1016/j.progpolymsci.2011.05.004Suche in Google Scholar

9. Barikani, M.Oliaei, E., Seddiqi, H. and Honarkar, H.: Preparation and application of chitin and its derivatives: a review; Iran Polym. J., 23 (2014) 307–326. 10.1007/s13726-014-0225-zSuche in Google Scholar

10. Iwatsubo, T., Kishi, R., Miura, T., Ohzono, T. and Yamaguchi, T.: Formation of Hydroxyapatite Skeletal Materials from Hydrogel Matrices via Artificial Biomineralization; J. Phys. Chem. B, 119 (2015) 8793–8799. 10.1021/acs.jpcb.5b03181Suche in Google Scholar PubMed

11. Vílchez, S., Samitier, V., Porras, M., Esquena, J. and Erra, P.: Chitosan Hydrogels Covalently Crosslinked with a Natural Reagent; Tenside Surf. Det.46 (2009)13–17. 10.3139/113.110002Suche in Google Scholar

12. Li, B., Liu, B., Shan, C., Ibrahim, M., Lou, Y., Wang, Y., Xie, G., Li, H-Y. and Sun, G.: Antibacterial activity of two chitosan solutions and their effect on rice bacterial leaf blight and leaf streak; Pest Manag. Sci., 69 (2013) 312–320. 10.1002/ps.3399Suche in Google Scholar

13. Wibowo, S., Velazquez, G., Savant, V., and Torres, J. A.: Effect of chitosan type on protein and water recovery efficiency from surimi wash water treated with chitosan–alginate complexes; Bioresour. Technol., 98 (2007) 539–545. 10.1016/j.biortech.2006.02.014Suche in Google Scholar

14. Ashori, A., Raverty, W. D., Vanderhoek, N. and Ward, J. V.: Surface topography of kenaf (Hibiscus cannabinus) sized papers; Bioresour. Technol., 99 (2008) 404–410. 10.1016/j.biortech.2006.12.011Suche in Google Scholar

15. Li, Z., Zhuang, X.P., Liu, X.F.Guan, Y.L. and Yao, K.D.: Study on antibacterial O-carboxymethylated chitosan/cellulose blend film from N,N-dimethylacetamide solution; Polymer, 43 (2002) 1541–1547. 10.1016/S0032-3861(01)00699-1Suche in Google Scholar

16. Kogan, G., Skorik, Y. A., Ingrid, I. Ž., Križková, L., Ďuračková, Z., Gomes, C.A.R.Yatluk, Y. and Krajčovič, J.: Antioxidant and antimutagenic activity of N-(2-carboxyethyl)chitosan; Toxicol Appl Pharmacol, 201 (2004) 303–310. 10.1016/j.taap.2004.05.009Suche in Google Scholar

17. Sajomsang, W., Tantayanon, S., Tangpasuthadol, V. and DalyW. H.: Quaternization of N-aryl chitosan derivatives: synthesis, characterization, and antibacterial activity; Carbohydr Res, 344 (2009) 2502–2511. 10.1016/j.carres.2009.09.004Suche in Google Scholar

18. Xu, Y., Du, Y., Huang, R. and Gao, L.: Preparation and modification of N-(2-hydroxyl) propyl-3-trimethyl ammonium chitosan chloride nanoparticle as a protein carrier; Biomaterials, 24 (2003) 5015–5022. 10.1016/S0142-9612(03)00408-3Suche in Google Scholar

19. Schatz, C., Bionaz, A., Lucas, J-M., Pichot, C., Viton, C., Domard, A. and DelairT.: Formation of Polyelectrolyte Complex Particles from Self-Complexation of N-Sulfated Chitosan; Biomacromolecules, 6 (2005) 1642–1647. 10.1021/bm049224qSuche in Google Scholar PubMed

20. Liu, X., Song, L., Li, L., Li, S. and Yao, K.: Antibacterial Effects of Chitosan and Its Water-Soluble Derivatives on E. coli, Plasmids DNA, and mRNA; J. Appl. Polym. Sci., 103 (2007) 3521–3528. 10.1002/app.25421Suche in Google Scholar

21. Liu, H., Zhao, Y., Cheng, S., Huang, N. and Leng, Y.: Syntheses of Novel Chitosan Derivative with Excellent Solubility, Anticoagulation, and Antibacterial Property by Chemical Modification; J. Appl. Polym. Sci., 124 (2012) 2641–2648. 10.1002/app.34889Suche in Google Scholar

22. Shao, K., Han, B., Dong, W., Liu, W. and Liu, W.: Pharmacokinetics and Biodegradation Performance of a Hydroxypropyl Chitosan Derivative; J. Ocean Univ. China, 14 (2015) 888–896. 10.1007/s11802-015-2600-6Suche in Google Scholar

23. Xu, X., Zhuang, X., Cheng, B., Xu, J., Long, G. and Zhang, H.: Manufacture and properties of cellulose/O-hydroxyethyl chitosan blend fibers; Carbohydr. Polym., 81 (2010) 541–544. 10.1016/j.carbpol.2010.03.011Suche in Google Scholar

24. Zhao, Y., Chen, J., Zeng, E., Hu, X., Liu, A. and DongY.: Synthesis and characterization of hydroxyethyl chitosan grafted by carboxyl ending DOVOB dendrimer: A novel liquid crystalline polymer; Carbohydr. Polym., 74 (2008) 828–833. 10.1016/j.carbpol.2008.04.042Suche in Google Scholar

25. Li, M., Han, B. and Liu, W.: Preparation and properties of a drug release membrane of mitomycin C with N-succinyl-hydroxyethyl chitosan; J Mater Sci: Mater Med, 22 (2011) 2745–2755. 10.1007/s10856-011-445-8Suche in Google Scholar

26. Huo, M., Liu, Y., Wang, L., Yin, T., Qin, C., Xiao, Y., Yin, L., Liu, J. and Zhou, J.: Redox-Sensitive Micelles Based on O,N-Hydroxyethyl Chitosan–Octylamine Conjugates for Triggered Intracellular Delivery of Paclitaxel; Mol. Pharmaceutics, 13 (2016) 1750–1762. 10.1021/acs.molpharmaceut.5b00696Suche in Google Scholar PubMed

27. Li, H., Huo, M., Zhou, J., Dai, Y., Deng, Y., Shi, X. and Masoud, J.: Enhanced Oral Absorption of Paclitaxel in N-Deoxycholic Acid-N, O-Hydroxyethyl Chitosan Micellar System; J. Pharm. Sci., 99 (2010) 4543–4553. 10.1002/jps.22159Suche in Google Scholar PubMed

28. Spinner, J. L., Oberoi, H. S., Yorgensen, Y. M., Poirier, D. S., Burkhart, D. J., Plante, M. and Evans, J. T.: Methylglycol chitosan and a synthetic TLR4 agonist enhance immuneresponses to influenza vaccine administered sublinguallyJustin; Vaccine, 33 (2015) 5845–5853. 10.1016/j.vaccine.2015.08.086Suche in Google Scholar PubMed PubMed Central

29. Jiang, S-M., Cai, Z-S., Chen, Z-D. and Xu, Q.: Synthesis of Dehydroabietyl Glycidyl Ether and Optimization of Synthetic Condition. Chem. World (Chinese), 55 (2014) 401–405. 10.19500/j.cnki.0367-6358.2014.08.011Suche in Google Scholar

30. Cai, Z-S., Jiang, S-M., Zhu, X-M., Zhang, H-H., Zhao, L-L., Yue, G-Y. and Shang, S-B.: (2-hydroxy-3-dehydroabieticoxy) propyl chitosan-oligosaccharide and preparation method thereof; Faming Zhuanli Shenqing Gongkai Shuomingshu (Chinese), (2016); CN 103965373 B.Suche in Google Scholar

31. Zhang, C., Ping, Q. and DingY.: Synthesis and Characterization of Chitosan Derivatives Carrying Galactose Residues; J. Appl. Polym. Sci., 97 (2005) 2161–2167. 10.1002/app.21975Suche in Google Scholar

32. Huang, R., Du, Y. and Yang, J.: Preparation and anticoagulant activity of carboxybutyrylated hydroxyethyl chitosan sulfates; Carbohydr. Polym., 51 (2003) 431–438. 10.1016/S0144-8617(02)00208-4Suche in Google Scholar

Received: 2018-10-07

Accepted: 2019-02-20

Published Online: 2019-05-06

Published in Print: 2019-05-15

Sie haben derzeit keinen Zugang zu diesem Inhalt.

Artikel in diesem Heft

https://doi.org/10.3139/113.110618

Schlagwörter für diesen Artikel

Polymeric nonionic surfactants; N,O-hydroxyethyl chitosan; Surface activities; Emulsifying property