Abstract
Chitosan (Ch), which is the result of the alkaline hydrolysis of the naturally occurring chitin biopolymer, is considered to be one of the highly versatile polymeric materials due to its active functional groups (–NH2 and –OH groups), biocompatibility, biodegradability, and nontoxic property. Preparation, analysis, and general properties of Ch and its derivatives have been reported in this chapter. Moreover, chemical modification of Ch by direct reactions on its active functional groups and by grafting technique has been discussed in details. Characterization of Ch and its carboxymethyl derivative (CMCh) grafted by various functionalized polymers has been carried out using spectral and thermal analyses, X-ray diffraction, and scanning electron microscopy. Various fields of applications of Ch and CMCh as superabsorbent materials, metal ions adsorption, ion exchangers, as well as in pharmaceutical and biomedical areas have been also discussed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
References
Pillai CKS, Paul W, Sharma CP (2009) Chitin and chitosan polymers: chemistry, solubility and fiber formation. Prog Polym Sci 34(7):641–678
Khor E (2002) Chitin: a biomaterial in waiting. Curr Opin Solid State Mater Sci 6(4):313–317
Van Luyen D, Dm H (1996) In: Salamone J (ed) Polymeric materials encyclopedia, vol 2. CRC, Boca Raton, FL, p 1208
Roja G, Floores JA, Rodriguez A, Ly M, Maldonado H (2005) Adsorption of chromium onto cross-linked chitosan. Sep Purif Technol 44:31–36
Peniche C, Argüelles-Monal W, Peniche H, Acosta N (2003) Chitosan: an attractive biocompatible polymer for microencapsulation. Macromol Biosci 3(10):511–520
Thanpitcha T, Sirivat A, Jamieson AM, Rujiravanit R (2006) Preparation and characterization of polyaniline/chitosan blend film. Carbohydr Polym 64(4):560–568
Varma AJ, Deshpande SV, Kennedy JF (2004) Metal complexation by chitosan and its derivatives: a review. Carbohydr Polym 55:77–93
Dutta PK, Tripathi S, Mehrotra CK, Dutta J (2009) Perspectives for chitosan based antimicrobial films in food applications. Food Chem 114:1173–1182
Bautista-Bănos S, Hermàdez-Lauzardo AN, Velàzquez-del Valle HG, Hermàdez-López M, Ait Barka E, Bosquez-Holina B et al (2006) Chitosan as a potential natural compound to control pre and postharvest diseases of horticultural commodities. Crop Prot 25:108–118
Kato Y, Onishi H, Hachida Y (2003) Application of chitin and chitosan derivatives in the pharmaceutical field. Curr Pharm Biotechnol 4:303–309
Rinaudo M (2006) Chitin and chitosan: properties and applications. Prog Polym Sci 31:603–632
Ma G, Yang D, Kennedy JF, Nie J (2009) Synthesize and characterization of organic-soluble acylated chitosan. Carbohydr Polym 75(3):390–394
Muzzarelli RAA, Rochetti R (1974) The determination of vanadium in sea water by hot graphite atomic absorption spectrometry on chitosan after separation from salt. Anal Chim Acta 70:283–289
**a YQ, Cuo TY, Song MD, Zhang BH, Zhang BL (2006) Selective separation of quercetin by molecular imprinting using chitosan beads as functional matrix. React Funct Polym 66:1734–1740
Sashiwa H, Aiba S (2004) Chemically modified chitin and chitosan as biomaterials. Prog Polym Sci 29:887–908
**e WM, Xu PX, Wang W, Liu Q (2002) Preparation and antimicrobial activity of a water-soluble chitosan derivative. Carbohydr Polym 50(1):35–40
Qu X, Wirsen A, Albertsson A (1999) Synthesis and characterization of pH-sensitive hydrogels based on chitosan and D, L-Lactic acid. J Appl Polym Sci 74:3193–3202
Guibal E, Touraud E, Roussy J (2005) The use of silver-coated ceramic beads for sterilization of Sphingomonas sp. in drinking mineral water. World J Microbiol Biotechnol 21(6–7):913–920
Li N, Bai R, Liu C (2005) Enhanced and selective adsorption of mercury ions on chitosan beads graftedwith polyarylamide via surface-initiated atom transfer radical polymerization. Langmuir 21(25):11780–11787
**aohui W, Yumin Du, Fei H, Hui L, Lihong F (2005) Abstract of papers. In: 22nd 9th ACS national meeting, San Diego, CA, USA, 13–17 March
Ju-Young Y, Hee-lack C, Tae S II, Young-Moo K, Wha-Jung K, Doo-Kyung M (2005) J Ind Eng Chem 11(6):957–963
Lacroix M, Le Thien C (2005) Edible films and coatings from non-starch polysaccharides. In: Han JH (ed) Innovations in food packagings. Elsevier, Amsterdam, pp 338–361
Broussignac P (1968) Chem Ind Geniechim 99:1242
Domard A, Rinaudo M (1983) Preparation and characterization of fully deacetylated chitosan. Int J Biol Macromol 5(1):49–52
Moore GK (1978) Ph.D. Thesis (CNAA), Trent Polytechic, UK
Hirai A, Odani H, Nakajima A (1991) Determination of degree of deacetylation of chitosan by 1H NMR spectroscopy. Polym Bull 26:87–94
Mourya VK, Inamdar NN (2008) Chitosan-modifications and applications opportunities galore. React Funct Polym 68:1013
Wolfrom ML, Maher GG, Chaney A (1957) Chitosan nitrate. J Org Chem 23:1990
Heras A, Rodrigues NM, Ramos VM, Agullo E (2001) N-methylene phosphonic chitosan: a novel soluble derivative. Carbohydr Polym 44:1–8
Ramos VM, Rodrygues NM, Dyaza MF, Rodrygues MS, Heras A, Agullo E (2003) N-methylene phosphonic chitosan. Effect of preparation methods on its properties. Carbohydr Polym 52:39–46
Matevosyan GL, Yukha YS, Zavlin PM (2003) Phosphorylation of chitosan. Russ J Gen Chem 73:1725–1728
Ramos VM, Rodrygues NM, Rodrygues MS, Heras A, Agullo E (2003) Modified chitosan carrying phosphonic and alkyl groups. Carbohydr Polym 51:425–429
Karrer P, Loenig H, Usteri E (1943) Zur Kenntnis blutgerinnungshemmender polysaccharide-poly-schwefelsaüre-ester und ähnlicher verbindungen. Helv Chim Acta 26:1296
Hackman RH (1954) Studies on Chitin I: enzymic degradation of chitin and chitin esters. Aust J Biol Sci 7:168–178
Coppick S, Hall WP (1947) In: Little RW (ed), Reinhold, New York, p 179
Katsuura K, Mizuno H (1966) Flame proofing of cotton fabrics with urea and phosphoric acid in organic solvent. Sen-1 Gakkishi 22(11):510–514
Sakaguchi T, Horikoshi T, Nakajima A (1981) Adsorption of uranium by chitin phosphate and chitosan phosphate. Agric Biol Chem 45(10):2191–2195
Laszkiewicz B (1985) Thermal properties of chitin ammonophosphates and their complexes with methanol. J Therm Anal Calorim 30(4):889–894
Nagasawa K, Tohira Y, Inoue Y, Tanoura N (1971) Reaction between carbohydrates and sulfuric acid: part I. Depolymerization and sulfation of polysaccharides by sulfuric acid. Carbohydr Res 18:95–102
Vikhoreva G, Bannikova G, Stolbushkina P, Panov A, Drozd N, Makarov V, Varlamov V, Galbraikh L (2005) Preparation and anticoagulant activity of a low-molecular-weight sulfated chitosan. Carbohydr Polym 62:327–332
Gamzazade A, Sklyar A, Nasibov S, Sushkov I, Shashkov A, Knirel Y (1997) Structural features of sulfated chitosans. Carbohydr Polym 34(1):113–116
Je JY, Park PJ, Kim SK (2005) Protyl endopeptidase inhibitory activity of chitosan sulfates with different degree of deacetylation. Carbohydr Polym 60(4):553–556
Zhang C, ** Q, Zhang H, Shen J (2003) Preparation of N-alkyl-O-sulfate chitosan derivatives and micellar solubilization of taxol. Carbohydr Polym 54(2):137–141
**ng R, Liu S, Yu H, Guo Z, Li Z, Li P (2005) Preparation of high-molecular weight and high-sulfate content chitosans and their potential antioxidant activity in vitro. Carbohydr Polym 61(2):148–154
**ng R, Liu S, Yu H, Zhang Q, Li Z, Li P (2004) Preparation of low-molecular-weight and high-sulfate-content chitosans under microwave radiation and their potential antioxidant activity in vitro. Carbohydr Res 339(5):2515–2519
Naggi AM, Torri G, Compagnoni T, Casu B (1986) In: Muzzarelli RAA, Jeuniaux C, Goody GW (eds) Chitin in nature and technology. Plenum, New York, NY, p 371
Shigemasa Y, Usui H, Morimoto M, Saimoto H, Okamoto Y, Minami S, Sashiwa H (1999) Chemical modification of chitin and chitosan 1: preparation of partially deacetylated chitin derivatives via a ring-opening reaction with cyclic acid anhydride in lithium chloride/N, N-dimethyl acetamide. Carbohydr Polym 39(3):237–243
Tien C, Lacroix M, Ispas-Szabo MMA (2003) N-Acetylated chitosan: hydrophobic matrices for controlled drug release. J Control Release 93:1–3
Sashiwa H, Kawasaki N, Nakayama A, Muraki E, Yamamoto N, Zhu H, Nagano H, Omura Y, Saimot H, Shigemasa Y, Aiba S (2002) Chemical modification of chitosan.13. Synthesis of organosoluble, palladium adsorbable and biodegradable chitosan derivatives towards the chemical plating on plastics. Biomacromolecules 3:1120–1125
Wu Y, Seo T, Maeda S, Sasaki T, Irie S, Sakurai K (2005) Circular dichroism induced by the helical conformations of acylated chitosan derivatives bearing cinnamate chromophores. J Polym Sci B Polym Phys 43:1354–1364
Hoffmann-La-Roche F and CO (1957) UK Patent 777: 204
Aiba S (1986) Studies on chitosan: 1. Determination of the degree of N-acetylation of chitosan by ultraviolet spectrophotometry and gel permeation chromatography. Int J Biol Macromol 8(3):173–176
Moore GK, Roberts GAF (1981) Reaction of chitosan: 2. Preparation and reactivity of N-acyl derivatives of chitosan. Int J Biol Macromol 3:292–296
Kurita K, Sannan T, Iwakura Y (1977) Studies on chitin, 3. Preparation of pure chitin, poly(N-acetyl-D-glucoseamine) from the water soluble chitin. Die Makromol Chem 178:2595–2602
Zhang C, ** Q, Zhang H, Shen J (2003) Synthesis and characterization of water soluble O-succinyl-chitosan. Eur Polym J 39:1629–1634
Moore GK, Roberts GAF (1982) Reactions of chitosan: 4. Preparation of organosoluble derivatives of chitosan. Int J Biol Macromol 4:246–249
Moore GK, Roberts GAF (1981) Reactions of chitosan: 3. Preparation and reactivity of Schiff’s base derivatives of chitosan. Int J Biol Macromol 3:337–341
Gupta KC, Jabrail FH (2007) Glutaraldehyde cross-linked chitosan microspheres for controlled released of centchroman. Carbohydr Res 342(15):2244–2252
Coelho TC, Laus RR, Mangrich AS, deFávere VT, Laranjeira CM (2007) Effect of heparin coating on epichlorohydrin cross-linked chitosan microspheres on the adsorption of copper (II) ions. React Funct Polym 67:468–475
Yisong Y, Wenjun L, Tongyin Y (1990) Polym Commun 31:319–321
Jamella SR, Jayakrishnan A (1995) Glutaraldehyde cross-linked chitosan microspheres as a long acting biodegradable drug delivery vehicle: studies on the in vitro release of mitoxantrone and in vivo degradation of microspheres in rat muscle. Biomaterials 16(10):769–775
Noguchi J (1963) (Asachi Chemical Industry Co., Ltd.) Japan 24, 400 (65), Oct 25, Appl. May 17, 3 pp
Lim S. “PhD thesis 2002” Faculty of North Carolina State University. “Synthesis of a fiber-reactive chitosan derivative and its application to fabricas an antimicrobial finish and a dyeing-improving agent.” (Under the direction of Sameul Mack Hudson).
Okimasu S (1958) Nippon Nogei Kagaku Kaishi 32:383
Plisko EA, Nud’ga LA, Danilov SN (1972) USSR Patent 325: 234
Nud’ga LA, Plisko EA, Danilov SN (1963) Zhur Obsch Khim 43:2752
Ge H, Luo D (2005) Preparation of carboxymethyl chitosan in aqueous solution under microwave irradiation. Carbohydr Res 340(7):1351–1356
Joshi JM, Sinha VK (2006) Graft copolymerization of 2-hydroxyethyl methacrylate onto carboxymethyl chitosan using CAN as an initiator. Polym J 47(6):2198–2204
Wu YG, Chan WL, Szeto YUS (2003) Preparation of O-carboxymethyl chitosan and their effect on color yield of acid dyes on silk. J Appl Polym Sci 90(9):2500–2502
Sugimoto M, Morimoto M, Sashiwa H (1998) Preparation and characterization of water-soluble chitin and chitosan derivatives. Carbohydr Polym 36(1):49–59
Jayakumar R, Prabaharan M, Reis RL, Mano JF (2005) Graft copolymerized chitosan—present status and applications. Carbohydr Polym 62:142–158
Wang J, Chen Y, Zhang S, Yu H (2008) A chitosan-based floculant prepared with gamma-irradiation-induced grafting. Bioresour Technol 99:3397–3402
Pengfei L, Maolin Z, Jilan W (2001) Study on radiation-induced grafting of styrene onto chitin and chitosan. Radiat Phys Chem 61(2):149–153
Mino G, Kaizerman S (1958) A new method for the preparation of graft copolymers. Polymerization initiated by ceric ion redox systems. J Polym Sci 31(122):242–243
Lagos A, Reyes J (1988) Grafting onto chitosan: 1. Graft copolymerization of methylmethacrylate onto chitosan with Fenton’s reagent (Fe2+–H2O2) as a redox initiator. Polym Sci A Polym Chem 26:985–991
Kataoka S, Ando T (1981) Molecular weight regulation in radical polymerization of methacrylic acid by chitosan. Kobunshi Ronbunshu 38(11):797–799
Athawale VD, Rathi SC (1999) Graft polymerization: starch as a model substrate. J Macromol Sci Rev Macromol Chem Phys C39(3):445–480
Berlin Ad A, Kislenko VN (1992) Kinetics and mechanism of radical graft polymerization of monomers onto polysaccharides. Prog Polym Sci 17:765–825
Pourjavada A, Mahdavinia GR, Zohuriaan-Mehr MJ (2003) Modified chitosan, II. H-ChitoPAN, a novel pH-responsive supersorbent hydrogel. J Appl Polym Sci 90:3115–3121
Poujavadi A, Zohuriaan-Mehr MJ, Mahdavinia GR (2004) Modified chitosan. III. Superabsorbency, salt- and pH-sensitivity of smart ampholytic hydrogels from chitosan-g-PAN. Polym Adv Technol 15(4):173–180
Mahdavinia GR, Pourjavadi A, Hosseinzadeh H, Zohuriaan MJ (2004) Modified chitosan. 4. Superabsorbent hydrogels from poly(acrylamide—co-acrylic acid) grafted chitosan with salt- and pH-responsiveness properties. Eur Polym J 40:1399
Jenkins DW, Hudson SM (2001) Review of vinyl graft copolymerization featuring recent advances towards controlled radical-based reactions and illustrated with chitin/chitosan trunk polymers. Chem Rev 101(11):3245–3274
Pourjavadi A, Mahdavinia GR, Zohuriaan-Mehr MJ, Omidian H (2003) Modified chitosan. I. Optimized cerium ammonium nitrate-induced synthesis of chitosan-g-polyacrylonitrile. J Appl Polym Sci 88(8):2048–2054
Yazdani-Pedram M, Lagos A, Retuert J, Guerrero R, Riquelme P (1995) On the modification of chitosan through grafting. J Macromol Sci Pure Appl Chem A32(5):1037–1047
Kataoka S, Ando T (1984) Radical polymerization of acrylic acid in the presence of chitosan. Kobunshi Ronbunshu 41(9):519–524
Wang Y, **gxinan Y, Kunyuan Q (1994) Studies of graft copolymerization onto chitosan. Acta Polymerica Sinica 2:188
Yazdani-Pedram M, Retuert J (1997) Homogeneous grafting reaction of vinyl pyrrolidone onto chitosan. J Appl Polym Sci 63(10):1321–1326
Retuert J, Yazdani-Pedram M (1993) Cocatalyst effect in potassium persulfate initiated grafting onto chitosan. Polym Bull 31(5):559–562
Akgün S, Ekici G, Mutlu N, Besirli N, Hazer B (2007) Synthesis and properties of chitosan—modified poly(vinyl butyrate). J Polym Res 14:215–221
Yazdani-Pedran M, Lagos A, Retuert PJ (2002) Study of the effect of reaction variables on grafting of polyacrylamide onto chitosan. Polym Bull 48:93–98
Mun GA, Nurkeeva ZS, Dergunov SA, Nam IK, Maimakov TP, Shaikhutdinov EM, Lee SC, Park K (2008) Studies on graft copolymerization of 2-hydroxyethyl acrylate onto chitosan. React Funct Polym 68:389–395
Zohuriaan-Mehr MJ (2005) Advances in chitin and chitosan modification through graft copolymerization: a comprehensive review. Iran Polym J 14(3):235–265
Liu YH, Shang YJ, Li WP, Wang Z, Deng KL (2000) Study on the kinetics of acrylonitrile polymerization initiated by diperiodatonickelate (IV) periodate complex. Acta Polymerica Sinica 2:235–238
Liu YH, Li WP, Deng KL (2001) Graft copolymerization of methyl acrylate onto nylon1010 initiated by potassium diperiodatonickelate (IV). J Appl Polym Sci 82(11):2636–2640
Ravi Kumar MNV, Muzzarelli RAA, Muzzarelli C, Sashiwa H, Domb AJ (2004) Chitosan chemistry and pharmaceutical perspectives. Chem Rev 104(12):6017–6084
Liu L, Wang YS, Shen XF, Fang YE (2005) Preparation of chitosan-g-polycaprolactone copolymers through ring-opening polymerization of ε-caprolactone onto phthaloyl-protected chitosan. Biopolymers 78(4):163–170
Guan XP, Quan DP, Shuai XT, Liao KR, Mai KC (2007) Chitosan-graft poly(ε-caprolactone)s: an optimized chemical approach leading to a controllable structure and enhanced properties. J Polym Sci A Polym Chem 45(12):2556–2568
Liu L, Chen LX, Fang YE (2006) Self-catalysis of phthaloylchitosan for graft copolymerization of e-caprolactone with chitosan. Macromol Rapid Commun 27(23):1988–1994
Wu Y, Zheng YL, Yang WL, Wang CC, Hu JH, Fu SK (2005) Synthesis and characterization of a novel amphiphilic chitosan-polylactide graft copolymer. Carbohydr Polym 59(2):165–171
Skotak M, Leonov AP, Larsen G, Noriega S, Subramanian A (2008) Biocompatible and biodegradable ultrafine fibrillar scaffold materials for tissue engineering by facile grafting of L-lactide onto chitosan. Biomacromolecules 9(7):1902–1908
Feng H, Dong CM (2006) Preparation, characterization, and self-assembled properties of biodegradable chitosan-poly(L-lactide) hybrid amphiphiles. Biomacromolecules 7(11):3069–3075
Fujioka M, Okada H, Kusaka Y, Nishiyama S, Noguchi H, Ishii S et al (2004) enzymatic synthesis of chitin- and chitosan-graft-aliphatic polyesters. Macromol Rapid Commun 25(20):1776–1780
Kurita K, Ikeda H, Yoshida Y, Shimojoh M, Harata M (2002) Chemoselective protection of the amino groups of chitosan by controlled phthaloylation: facile preparation of a precursor useful for chemical modifications. Biomacromolecules 3(1):1–4
Makuška R, Gorochovceva N (2006) Regioselective grafting of poly(ethylene glycol) onto chitosan through C-6 position of glucosamine units. Carbohydr Polym 64(2):319–327
Cai G, Jiang H, Chen Z, Tu K, Wang L, Zhu K (2009) Synthesis, characterization and self assemble behavior of chitosan-O-poly(ε-caprolactone). Eur Polym J 45:1674–1680
Cai GQ, Jiang HL, Tu KH, Wang LQ, Zhu KJ (2009) A facile route for regioselective conjugation of organo-soluble polymers onto chitosan. Macromol Biosci 9(3):256–261
Li Z, Guo J, Zhang J, Zhao Y, Lv L, Ding C, Zhang X (2010) Chitosan-graft-polyethylenimine with improved properties as a potential gene vector. Carbohydr Polym 80(1):254–259
Duan W, Chen C, Jiang L, Li GH (2008) Preparation and characterization of the graft copolymer of chitosan with poly[rosin-(2-acryloyloxy)ethyl ester]. Carbohydr Polym 73(4):582–586
Mohamed RR, Sabaa MW (2010) Graft copolymerization of acrylonitrile and its amidoxime derivative onto chitosan. J Appl Polym Sci 116:413–421
Sabaa MW, Mohamed NA, Ali R, Abd El Latif SM (2010) Chemically induced graft copolymerization of acrylonitrile onto carboxymethyl chitosan and its modification to amidoxime derivative. Polym Plast Technol Eng 49:1055–1064
Huacai G, Wan P, Dengke L (2006) Graft copolymerization of chitosan with acrylic acid under microwave irradiation and its water absorbency. Carbohydr Polym 66:372–378
Liu G, Zhai Y, Wang X, Wang W, Pan Y, Dong X, Wang Y (2008) Preparation, characterization, and in vitro drug release behavior of biodegradable chitosan-graft-poly(1,4-dioxan-2-one) copolymer. Carbohydr Polym 74(4):862–867
Detchprohm S, Aoi K, Okada M (2001) Synthesis of a novel chitin derivative having oligo(ε-caprolactone) side chains in aqueous reaction media. Macromol Chem Phys 202:3560–3570
Zhong Z, Kimura Y, Takahashi M, Yamane H (2000) Characterization of chemical and solid state structures of acylated chitosans. Polymer 41:899–906
Liu L, Xu X, Guo S, Han W (2009) Synthesis and self-assembly of chitosan-based copolymer with a pair of hydrophobic/hydrophilic grafts of polycaprolactone and poly(ethylene glycol). Carbohydr Polym 75:401–407
Kang H, Cai Y, Liu P (2006) Synthesis, characterization and thermal sensitivity of chitosan-based graft copolymers. Carbohydr Res 341:2851–2857
ElKhholy SS, Khalil KD, Elsabee MZ (2011) Grafting of acryloyl cyanoacetohydrazide onto chitosan. J Polym Res 18:459–467
Mum GA, Nurkeeva ZS, Dergunov SA, Nam IK, Maimakov TP, Shaikhutdinov EM, Lee SC, Park K (2008) Studies on graft copolymerization of 2-hydroxyethyl acrylate onto chitosan. React Funct Polym 68:389–395
Sabaa MW, Mohamed NA, Mohamed RR, Khalil NM, Abd El Latif MS (2010) Synthesis, characterization and antimicrobial activity of poly (N-vinylimidazole) grafted carboxymethyl chitosan. Carbohydr Polym 79:998–1005
El-Sherbiny IM, Smyth HDC (2010) Biodegradable nano-micro carrier systems for sustained pulmonary drug delivery: (I) self-assembled nanoparticles encapsulated in respirable/swellable semi-IPN microspheres. Int J Pharm 395:132–141
Yu C, Yun-fei L, Hui-min T, Jian-xin J (2009) Synthesis and characterization of a novel superabsorbent polymer of N, O-carboxymethyl chitosan graft copolymerized with vinyl monomers. Carbohydr Polym 75:287–292
Omidian H, Rocca JC, Park K (2005) Advances in superporous hydrogels. J Control Release 102:3–12
Liu JH, Wang Q, Wang AQ (2007) Synthesis and characterization of chitosan-g-poly(acrylic acid)sodium humate superabsorbent. Carbohydr Polym 70:166–173
Sun LP, Du YM, Shi XW, Chen X, Yang JH, Xu YM (2006) A new approach to chemically modified carboxymethyl chitosan and study of its moisture-absorption and moisture-retention abilities. J Appl Polym Sci 102:1303–1309
Pang HT, Cheng XG, Park HJ, Cha DS, Kennedy JF (2007) Preparation and rheological properties of deoxycholate-chitosan and carboxymethyl chitosan in aqueous systems. Carbohydr Polym 69:419–425
Babel S, Kurniawan TA (2003) Low-cost adsorbents for heavy metals uptake from contaminated water: a review. J Hazard Mater 97(1–3):219–243
Guibal E (2004) Interaction of metal ions with chitosan-based sorbents: a review. Sep Purif Technol 38(1):43–74
Chen XG, Park HJ (2003) Chemical characteristics of O-carboxymethyl chitosans related to the preparation conditions. Carbohydr Polym 53(4):355–359
Hon DNS, Tang LG (2000) Chelation of chitosan derivatives with zinc ions. I. O, N-carboxymethyl chitosan. J Appl Polym Sci 77(10):2246–2253
Farag S, Kareem SSA (2009) Different natural biomasses for lead cation removal. Carbohydr Polym 78(2):263–267
Sousa KS, Silva EC, Airoldi C (2009) Ethylenesulfide as a useful agent for incorporation into the biopolymer chitosan in a solvent-free reaction for use in cation removal. Carbohydr Res 344(13):1716–1723
Emara AAA, Tawab MA, El-ghamry MA, Elsabee MZ (2011) Metal uptake by chitosan derivatives and structure studies of the polymer metal complex. Carbohydr Polym 83:192–202
Jiang J, Hua D, Jiang J, Tang J, Zhu X (2010) Synthesis and property of poly(sodium 4-styrenesulfonate) grafted chitosan by nitroxide-mediated polymerization with chitosan-TEMPO macroinitiator. Carbohydr Polym 81:358–364
Muzzarelli RAA (1973) Analytical application of chitin and chitosan. In: Belcher R, Freiser H (eds) Natural chelating polymers; alginic acid, chitin and chitosan. Pergamon Press, New York, NY, pp 177–227
Singh V, Tripathi DN, Tiwari A, Sanghi R (2006) Microwave synthesized chitosan-graft-poly(methylmethacrylate): an efficient Zn+ ion binder. Carbohydr Polym 65(1):35–41
El-Sherbiny IM (2009) Synthesis, characterization and metal uptake capacity of a new carboxymethyl chitosan derivative. Eur Polym J 45:199–210
Mintzer MA, Simanek EE (2009) Nonviral vectors for gene delivery. Chem Rev 109:259–302
Nguyen DN, Green JJ, Chan JM, Langer R, Anderson DC (2009) Polymeric materials for gene delivery and DNA vaccination. Adv Mater 21(16):847–867
Hussain SM, Braydich-Stolle LK, Schrand AM, Murdock RC, Yu KO, Mattie DM et al (2009) Toxicity evaluation for safe use of nanomaterials: recent achievements and technical challenges. Adv Mater 21(16):1549–1559
Mumper RJ, Wang J, Claspell JM, Rolland AP (1995) Novel polymeric condensing carriers for gene delivery. In: Proceedings of the international symposium on controlled release of bioactive materials, vol 22, p 178
Liu WG, Yao KD (2002) Chitosan and its derivatives—a promising non-viral vector for gene transfection. J Control Release 83(1):1–11
Jiang HL, Kim YK, Arote R, Nah JW, Cho MH, Choi YJ et al (2007) Chitosan-graft-polyethylenimine as a gene carrier. J Control Release 117(2):273–280
Lu B, Xu XD, Zhuo RX, Cheng SX, Zhuo RX (2008) Low molecular weight polyethylenimine grafted N-maleated chitosan for gene delivery: properties and in vitro transfection studies. Biomacromolecules 9:2594
Wong K, Sun G, Zhang X, Dai H, Liu Y, He C, Leong KW (2006) PEI-g-chitosan, a novel gene delivery system with transfection efficiency comparable to polyethylenimine in vitro and after liver administration in vivo. Bioconjug Chem 17(1):152–158
Kunath K, Von Harpe A, Fischer D, Petersen H, Bickel U, Voigt K, Kissel T (2003) Low-molecular-weight polyethylenimine as a non-viral vector for DNA delivery: comparison of physicochemical properties, transfection efficiency and in vivo distribution with high-molecular-weight polyethylenimine. J Control Release 89(1):113–125
Neu M, Fischer D, Kissel T (2005) Recent advances in rational gene transfer vector design based on poly(ethylene imine) and its derivatives. J Gene Med 79(8):992–1009
Jeong JH, Kim SW, Park TG (2007) Molecular design of functional polymers for gene therapy. Prog Polym Sci 32(11):1239–1274
Kircheis R, Wightman L, Wagner E (2001) Design and gene delivery activity of modified polyethylenimines. Adv Drug Deliv Rev 53(3):341–358
El-Sherbiny IM, Smyth HDC (2012) Controlled release pulmonary administration of curcumin using swellable biocompatible microparticles. Mol Pharm 9:269–280
Zhong Z, **ng R, Liu S, Wang L, Cai S, Li P (2008) Synthesis of acyl thiourea derivatives of chitosan and their antimicrobial activities in vitro. Carbohydr Res 343(3):566–570
Wang X, Huang Y, Zhu J, Pan Y, He R, Wang Y (2009) Chitosan-graft poly(p-dioxanone) copolymers: preparation, characterization, and properties. Carbohydr Res 344(6):801–807
He R, Wang X, Wang Y, Yang K, Zeng J, Ding S (2006) A study on grafting poly(1,4-dioxan-2-one) onto starch via 2,4-toluene diisocyanate. Carbohydr Polym 65(1):28–34
El-Sherbiny IM, Smyth HDC (2010) Poly(ethylene glycol)–carboxymethyl chitosan-based pH-responsive hydrogels: photo-induced synthesis, characterization, swelling, and in vitro evaluation as potential drug carriers. Carbohydr Res 345(14):2004–2012
Calvo P, Remunan-lopez C, Vila-Jato JL, Alonso MJ (1997) Novel hydrophilic chitosan-polyethylene oxide nanoparticles as protein carriers. J Appl Polym Sci 63:125–132
Giunchedi P, Genta B, Muzzarelli RAA, Conte U (1998) Preparation and characterization of ampicillin loaded methylpyrrolidinone and chitosan microspheres. Biomaterials 19:157–161
Borchard G, Lueben HL, De Boer GA, Verhoef JC, Lehr CM, Junginger HE (1996) The potential of mucoadhesive polymers in enhancing intestinal peptide drug absorption. III. Effects of chitosan-glutamate and carbomer on epithelial tight junctions in vitro. J Control Release 39(2–3):131–138
Richardson SCW, Kolbe HVJ, Duncan R (1999) Potential of low molecular mass chitosan as a DNA delivery system: biocompatibility, body distribution and ability to complex and protect DNA. Int J Pharm 178:231–243
Janes KA, Calxo P, Alonso MJ (2001) Polysaccharide colloidal particles as delivery systems for macromolecules. Adv Drug Deliv Rev 47:83–97
Thanou MM, Kotze´ AF, Scharringhausen T, Lueكen HL, De Boer AG, Verhoef JC et al (2000) Effect of degree of quaternization of N-trimethyl chitosan chloride for enhanced transport of hydrophilic compounds across intestinal Caco-2 cell monolayers. J Control Release 64(1–2):15–25
Xu YM, Du YM, Huang RH, Gao LP (2003) Preparation and modification of N-(2-hydroxyl) propyl-3-trimethyl ammonium chitosan chloride nanoparticle as a protein carrier. Biomaterials 24:5015–5022
Amiji MM (1997) Synthesis of anionic poly(ethylene glycol) derivative for chitosan surface modification in blood-contacting applications. Carbohydr Polym 32(3–4):193–199
Choksakulnimitr S, Masuda S, Tokuda H, Takakura Y, Hashida M (1995) In vitro cytotoxicity of macromolecules in different cell culture systems. J Control Release 34(3):233–241
Fischer D, Li Y, Ahlemeyer B, Krieglstein J, Kissel T (2003) In vitro cytotoxicity testing of polycations: influence of polymer structure on cell viability and hemolysis. Biomaterials 24:1121–1131
Gerf R, Minamitake Y, Perracchia MT, Trubetskoy V, Torchilin V, Langer R (1994) Biodegradable long-circulating polymeric nanospheres. Science 263:1600–1603
Peracchia MT, Gref R, Minamitake Y, Domb A, Lotan N, Langer R (1997) PEG-coated nanoparticles from amphiphilic diblock and multiblock copolymer: investigate of their encapsulation and release characteristics. J Control Release 46(3):223–231
Quellec P, Gref R, Perrin L, Dellacherie E, Sommer F, Verbavatz JM et al (1998) Protein encapsulation within polyethylene glycol-coated nanospheres. I. Physicochemical characterization. J Biomed Mater Res 42:45–54
Hu Y, Jiang XQ, Ding Y, Zhang LY, Yang CZ, Zhang JF et al (2003) Preparation and drug release be hehaviors of nimodipine- loaded poly(caprolactone)-poly(ethylene oxide)-polylactide amphiphilic copolymer nanoparticles. Biomaterials 24:2395–2404
Qin Y, **ng R, Liu S, Li K, Meng X, Li R, Cui J, Li B, Li P (2012) Novel thiosemicarbazone chitosan derivatives: preparation, characterization, and antifungal activity. Carbohydr Polym 87:2664–2670
Mohamed RR, Seoudi RS, Sabaa MW (2012) Synthesis and characterization of antibacterial semi-interpenetrating carboxymethyl chitosan/poly(acrylonitrile) hydrogels. Cellulose 19(3):947–958
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Sabaa, M.W. (2013). Chitosan-g-Copolymers: Synthesis, Properties, and Applications. In: Kalia, S., Sabaa, M. (eds) Polysaccharide Based Graft Copolymers. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-36566-9_4
Download citation
DOI: https://doi.org/10.1007/978-3-642-36566-9_4
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-36565-2
Online ISBN: 978-3-642-36566-9
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)