Preparation, swelling and antibacterial behaviors of N-succinyl chitosan-g-poly(acrylic acid-co-acrylamide) superabsorbent hydrogels

Abstract

Superabsorbent hydrogels were prepared successfully from N-succinyl chitosan grafted poly(acrylic acid-co-acrylamide). The potassium persulfate (KPS), N, N’-methylenebisacrylamide (MBA) were used as the initiator and crosslinker, respectively. Fourier transform infrared spectroscopy (FTIR) and scanning electron microscopy (SEM) were used to confirm the porous network structure of superabsorbent hydrogel. The effects of reaction parameters on the swelling behaviors of the superabsorbent hydrogels were investigated. The results indicated that water absorbency increased first, and then decreased gradually with the increase in the contents of monomer (AA+AM), KPS, MBA or acrylamide. The product had excellent water absorbency of 1375 g/g in distilled water and 83 g/g in 0.9wt% NaCl solution. Simultaneously, the superabsorbent hydrogels were pH sensitive. The antibacterial activities of the hydrogels against Escherichia coli (E. coli) were improved effectively because of polyamidoamine (PAMAM) dendrimer absorbed in the hydrogels.

Keywords

superabsorbent hydrogels / N-succinyl chitosan / water absorbency / PAMAM dendrimer / antibacterial activity

References

[1] Chang CY, Duan B, Cai J, et al. Superabsorbent Hydrogels based on Cellulose for Smart Swelling and Controllable Delivery[J]. Eur. Polym. J., 2010, 46(1): 92-100.

[2] Witono JR, Noordergraaf IW, Heeres HJ, et al. Water Absorption, Retention and the Swelling Characteristics of Cassava Starch Grafted with Polyacrylic Acid[J]. Carbohydr. Polym., 2014, 103: 325-332.

[3] Tang H, Chen H, Duan B, et al. Swelling Behaviors of Superabsorbent Chitin/Carboxymethylcellulose Hydrogels[J]. J. Mater. Sci., 2014, 49(5): 2235-2242.

[4] Huang ZH, Liu SX, Zhang B, et al. Preparation and Swelling Behavior of a Novel Self-Assembled β-Cyclodextrin/Acrylic Acid/Sodium Alginate Hydrogel[J]. Carbohydr. Polym., 2014, 113: 430-437.

[5] Wan T, Xiong L, Huang RQ, et al. Properties and Structure of Microcrystal Muscovite Composite Superabsorbent[J]. J. Wuhan Univer. Technol. -Mater. Sci. Ed., 2014, 29(6): 1302-1306.

[6] Ge HC, Wang SK. Thermal Preparation of Chitosan-Acrylic Acid Superabsorbent: Optimization, Characteristic and Water Absorbency[J]. Carbohydr. Polym., 2014, 113: 296-303.

[7] Ghasemzadeh H, Ghanaat F. Antimicrobial Alginate/PVA Silver Nanocomposite Hydrogel, Synthesis and Characterization[J]. J. Polym. Res., 2014, 21: 355.

[8] Yan CY, Chen DW, Gu JW, et al. Preparation of N-Succinyl-Chitosan and Their Physical-Chemical Properties as a Novel Excipient[J]. Yakugaku zasshi: J. Pharm., 2006, 126(9): 789-793.

[9] Xiong WY, Yi Y, Liu HZ, et al. Selective Carboxypropionylation of Chitosan: Synthesis, Characterization, Blood Compatibility, and Degradation[J]. Carbohydr. Res., 2011, 346(10): 1217-1223.

[10] Ying GQ, Yang H, Yi Y, et al. Relationships between the Molecular Structure and Moisture-Absorption and Moisture-Retention Abilities of Succinyl Chitosan[J]. Polym. Bull., 2007, 59(4): 509-516.

[11] Huang XY, Bu HT, Jiang GB, et al. Cross-Linked Succinyl Chitosan as an Adsorbent for the Removal of Methylene Blue from Aqueous Solution[J]. Int J. Biol. Macromol., 2011, 49(4): 643-651.

[12] Li Q, Zhao YH, Wang L, et al. Adsorption Characteristics of Methylene Blue onto the N-Succinyl-Chitosan-g-Polyacrylamide/Attapulgite Composite[J]. Korean J. Chem. Eng., 2011, 28(8): 1658-1664.

[13] Sun SL, Wang AQ. Adsorption Properties of N-Succinyl-Chitosan and Cross-Linked N-Succinyl-Chitosan Resin with Pb(II) as Template Ions[J]. Sep. Purif.Technol., 2006, 51(3): 409-415.

[14] Zeng R, Wang ZH, Wang HR, et al. Preparation, Characterization and in Vitro Release of Chitosan-Stavudine Conjugate Nano-Prodrug[J]. J. Wuhan Univer. Technol.-Mater. Sci. Ed., 2013, 28(3): 617-621.

[15] Sun JC, Xiao C, Tan HP, et al. Covalently Crosslinked Hyaluronic Acid-Chitosan Hydrogel Containing Dexamethasone as an Injectable Scaffold for Soft Tissue Engineering[J]. J. Appl.Polym. Sci., 2013, 129: 682-688.

[16] Fan LH, Yu L, Xu YM, et al. The Novel Alginate/N-Succinyl-Chitosan Antibacterial Blend Fibers[J]. J. Appl. Polym. Sci., 2010, 116(4): 2151-2156.

[17] Cheng YY, Qu HO, Ma ML, et al. Polyamidoamine (PAMAM) Dendrimers as Biocompatible Carriers of Quinolone Antimicrobials: an in Vitro Study[J]. Eur. J. Med. Chem., 2007, 42(7): 1032-1038.

[18] Lu Y, Slomberg DL, Shah A, et al. Nitric Oxide-Releasing Amphiphilic Poly(Amidoamine) (PAMAM) Dendrimers as Antibacterial Agents[J]. Biomacromolecules, 2013, 14(10): 3589-3598.

[19] Wróblewska M, Winnicka K. The Effect of Cationic Polyamidoamine Dendrimers on Physicochemical Characteristics of Hydrogels with Erythromycin[J]. Int. J. Mol. Sci., 2015, 16(9): 20277-20289.

[20] Xue XY, Mao XG, Li Z, et al. A Potent and Selective Antimicrobial Poly(Amidoamine) Dendrimer Conjugate with LED209 Targeting QseC Receptor to Inhibit the Virulence Genes of Gram Negative Bacteria[J]. Nanomedicine: Nanotechnol., Bio. Med., 2015, 11(2): 329-339.

[21] Xue XY, Chen XQ, Mao XG, et al. Amino-Terminated Generation 2 Poly(Amidoamine) Dendrimer as a Potential Broad-Spectrum, Nonresistance-Inducing Antibacterial Agent [J]. AAPS. J., 2013, 15(1): 132-142.

[22] Wu F, Zhang Y, Liu L, et al. Synthesis and Characterization of a Novel Cellulose-g-Poly(Acrylic Acid-co-Acrylamide) Superabsorbent Composite Based On Flax Yarn Waste[J]. Carbohydr. Polym., 2012, 87(4): 2519-2525.

[23] Xu XB, Lü SY, Gao CM, et al. Facile Preparation of pH-Sensitive and Self-Fluorescent Mesoporous Silica Nanoparticles Modified with PAMAM Dendrimers for Label-Free Imaging and Drug Delivery[J]. Chem. Eng. J., 2015, 266: 171-178.

[24] Jung J, Zhao YY. Impact of the Structural Differences Between α- and β-Chitosan on Their Depolymerizing Reaction and Antibacterial Activity[J]. J. Agr. Food Chem., 2013, 61(37): 8783-8789.

[25] Wang ZK, Hu QL. Chitosan Rods Reinforced by N-Carboxyl Propionyl Chitosan Sodium[J]. Acta Phys. -Chim. Sin., 2010, 26(07): 2053-2056.

[26] Li Q, Ma ZH, Yue QY, et al. Synthesis, Characterization and Swelling Behavior of Superabsorbent Wheat Straw Graft Copolymers[J]. Bioresour. Technol., 2012, 118: 204-209.

[27] Ma ZH, Li Q, Yue QY, et al. Synthesis and Characterization of a Novel Super-Absorbent Based on Wheat Straw[J]. Bioresour. Technol., 2011, 102(3): 2853-2858.

[28] Xie YT, Wang AQ. Study on Superabsorbent Composites XIX. Synthesis, Characterization and Performance of Chitosan-g-Poly (Acrylic Acid)/Vermiculite Superabsorbent Composites[J]. J. Polym Res., 2009, 16(2): 143-150.

[29] Pourjavadi A, Harzandi AM, Hosseinzadeh H. Modified Carrageenan 3. Synthesis of a Novel Polysaccharide-Based Superabsorbent Hydrogel via Graft Copolymerization of Acrylic Acid onto Kappa-Carrageenan in Air[J]. Eur. Polym. J., 2004, 40(7): 1363-1370.

[30] Pourjavadi A, Barzegar S, Mahdavinia GR. MBA-Crosslinked Na-Alg/CMC as a Smart Full-Polysaccharide Superabsorbent Hydrogels[J]. Carbohydr. Polym., 2006, 66(3): 386-395.

[31] Wu L, Liu MZ. Slow-Release Potassium Silicate Fertilizer with the Function of Superabsorbent and Water Retention[J]. Ind. Eng. Chem. Res., 2007, 46(20): 6494-6500.

[32] Zhang YH, Wang LM, Li XH, et al. Salt-Resistant Superabsorbents from Inverse-Suspension Polymerization of PEG Methacrylate, Acryamide and Partially Neutralized Acrylic Acid[J]. J. Polym. Res., 2011, 18(2): 157-161.

[33] Chen ZB, Liu MZ, Ma SM. Synthesis and Modification of Salt-Resistant Superabsorbent Polymers[J]. React. & Funct. Polym., 2005, 62(1): 85-92.

[34] Wang WB, Wang AQ. Synthesis and Swelling Properties of pHSensitive Semi-IPN Superabsorbent Hydrogels Based on Sodium Alginate-g-Poly(Sodium Acrylate) and Polyvinylpyrrolidone[J]. Carbohydr. Polym., 2010, 80(4): 1028-1036.

[35] Lanthong P, Nuisin R, Kiatkamjornwong S. Graft Copolymerization, Characterization, and Degradation of Cassava Starch-g-Acrylamide/Itaconic Acid Superabsorbents[J]. Carbohydr. Polym., 2006, 66(2): 229-245.

[36] Winnicka K, Wroblewska M, Wieczorek P, et al. The Effect of PAMAM Dendrimers on the Antibacterial Activity of Antibiotics with Different Water Solubility[J]. Molecules, 2013, 18(7): 8607-8617.

[37] Wei QB, Fu F, Zhang YQ, et al. Preparation, Characterization, and Antibacterial Properties of pH-Responsive P(MMA-co-MAA)/Silver Nanocomposite Hydrogels[J]. J. Polym. Res., 2014, 21: 349.