Antibacterial property of fabric treated with a fiber-reactive chitosan derivative

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1 Journal of Textile Research Vol. 32 No. 2 Fen % CTS N- HDCC HDCC N- NMA O- -N- NMA-HDCC HDCC NMA-HDCC 95% HDCC 100% 30 NMA-HDCC 85% NMA-HDCC 2 g / L min TS A Antibacterial property of fabric treated with a fiber-reactive chitosan derivative PAN Hong 1 ZHAO Tao College of Chemistry Chemical Engineering & Biotechnology Donghua University Shanghai China 2. Key Laboratory of Science & Technology of Eco-Textile Ministry of Education Donghua University Shanghai China Abstract N-hydroxypropyl lauryl dimethyl ammonium chloride chitosan HDCC was prepared by introducing epoxypropyl lauryl dimethyl ammonium chloride to the amino-group of chitosan CTS with a degree of deacetylation about 85% and then HDCC with good water solubility was crosslinked with N- hydroxymethyl acrylamide NMA thus obtained the end product of a novel chitosan derivative O- acrylamidomethyl-n- 2-hydroxy-3-dodecyl ammonium propyl chitosan chloride NMA-HDCC that can form covalent bond with cellulosic fiber. The antibacterial experiment demonstrated that the cotton fabrics treated with CTS HDCC and NMA-HDCC all showed above 95% bacteria inhibiting ratio against Bacillus coli and HDCC in particular showed nearly 100%. After 30 washing cycles the cotton fabric treated by NMA-HDCC exhibited above 85% bacteria inhibiting ratio though those treated by CTS chitosan quaternary ammonium salt exhibited little effect. For durable antibacterial effect the optimal process conditions for treating cotton fabrics with NMA-HDCC were determined as follows mass concentration of finishing agent 2 g / L curing at 140 for 5 min. Key words chitosan quaternary ammonium salt modification antibacterial property washing durability ZR tzhao@ dhu. edu. cn

2 2 97 CTS FT-IR Nicolet Magna-IR ATLAS DZF-1 8 THZ-C- 1 YXQ- IS-50S11 KYC ph 100B BS-1E Excel SPX-105B 1. 3 Tsurugai K 9 N N N NMA-HDCC N- Kim 10 1 h h h N- HDCC 2 g 85 1 h NMA 11 O- -N- 1 h 7 g 7 h NMA-HDCC ph 24 h tex tex 524 /10 cm 284 /10 cm NMA-HDCC 1. 2 g HDCC 4. 6 g NMA g g NH 4 Cl min 15 ml 100 ml 95% Acros 1 1 Organics 80 N- 1 HTCC O- -N NMA-HDCC NMA-HTCC 2 NMA-HDCC 11 N- β-c 85. 7%

3 Fig. 1 NMA-HDCC Preparation of NMA-HDCC Fig. 2 2 NMA-HDCC Reaction of NMA-HDCC with cotton fiber NMA-HDCC OH - 5 min g 2 g / L 1% NaHCO 3 20 g / L 2. 1 NMA-HDCC NMA-HDCC 100 ml 85% 70 4 min min 6 min NMA-HTCC NMA-HDCC h r / s 0. 1 ml 9. 9 ml 10 5 ~ ~ 15 ml 1 ml 20 mm 37 1 d 2 AATCC R = B - A / B 100% R B A min 2 min KBr IR cm - 1 CH 3 CH cm - 1 CH 2 n cm - 1 C O

4 Fig. 3 IR Infra-red spectrum IR of epoxypropyl dodecyl dimethyl quaternary ammonium salt NMA-HDCC KBr CTS HDCC NMA-HDCC IR HTCC 24 h Tab. 1 1 Inhibitory ratios of cotton fibers treated with different antibacterial agents / % HTCC HDCC NMA-HTCC NMA-HDCC Fig. 4 CTS HDCC NMA-HDCC IR Comparison of IR spectra between CTS HDCC and NMA-HDCC CTS HDCC CTS cm - 1 CTS N H cm - 1 CH 3 C H cm - 1 CTS cm - 1 O H N cm - 1 N H cm - 1 O H NMA-HDCC cm - 1 C O cm - 1 C C NMA-HDCC NMA HDCC 1 95% NMA-HDCC

5 g / L NMA-HDCC 2 g / L HDCC HTCC 2 g / L 5 min 6 NMA-HDCC NMA-HTCC NMA-HDCC NMA- HTCC 2. 3 NMA-HDCC 30 85% 70 4 min Fig NMA-HDCC min 140 NMA-HDCC 120 NMA-HDCC Effect of baking temperature on antibacterial durability g / L NMA-HDCC Fig. 5 Effect of concentration of NMA-HDCC on antibacterial durability 5 2 g / L NMA-HDCC NMA-HDCC NMA-HDCC 7 NMA-HDCC Fig. 7 Effect of baking time on antibacterial durability

6 ZHANG Wei LIN Hong CHEN Yuyue. The application and the development foreground of chitin and chitosan J. Journal of Nantong University Natural Science Edition min 2 MUZZARELLI R JEUNIAUX C GOODAY G W. Chitin in Nature and Technology M. New York 3 1 HDCC HTCC Macmillan Press Ltd l GOOSEN M F A. Applications of Chitin and Chitosan M. Lancaster PA Technomic Publishing NMA-HDCC NMA-HTCC 95% MUZZARELLI R A A PETER M G. Chitin Handbook M. Grottammare Atec Edizioni ph 6. M JIANG T D. Chitin M. Beijing China Environmental NMA-HDCC NMA-HTCC Science Press PETER M G. Applications and environmental aspects of HDCC HTCC chitin and chitosan J. J Mol Sci Pure Appl Chem J MA Ning WANG Qin SUN Shengling et al. Progress 3 HDCC HTCC in chemical modification of chitin and chitosan J. HDCC HTCC Progress in Chemistry NMA-HDCC 9 TSURUGAI K. Preparation and antibacterial activity of NMA-HTCC N-trimethylammonium salts of chitosan J. Sen-I 4 NMA-HDCC 2 g / L min 11 SANG H L SAMUEL M H. Synthesis and antimicrobial activity of a water-soluble chitosan derivative FZXB Plenum Press ROBERTS G A F. Gakkaishi Chitin Chemistry M. London 10 KIM C H. Synthesis of chitosan derivatives with quaternary ammonium salt and their antibacterial activity J. Polymer Bulletin with a fiber-reactive group J. Carbohydrate Research SANG H L SAMUEL M. H. Application of a fiber- 1. reactive chitosan derivative to cotton fabric as an J antimicrobial textile finish J. Carbohydrate Polymers

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