Synthesis of a quaternary ammonium derivative of chito-oligosaccharide as antimicrobial agent for cellulosic fibers

Abstract

A derivative of chito-oligosaccharide (COS), N-(2-hydroxyl)propyl-3-trimethyl ammonium chito-oligosaccharide chloride (HTACC), was synthesized using a reaction of glycidyltrimethylammonium chloride (GTMAC) and COS prepared by depolymerization of a fully deacetylated chitosan. COS and HTACC were applied to the cotton fabrics with a pad-dry-cure process using the reaction between the hydroxyl group of cellulose and terminal aldehyde group in COS and HTACC. Their minimum inhibition concentration (MIC) was evaluated, and the antimicrobial activity and durability to laundering of cotton fabrics treated with them were compared. The complete substitution of NH 2 groups in COS with GTMAC was obtained at a 4 : 1 mol ratio of GTMAC to NH 2 in 18 h at 80°C under the presence of acetic acid. MIC values of the 1.04 DS of HTACC and COS were 50 and 400 g/mL, respectively. A cotton fabric treated with 0.2% of HTACC and 1.8% of COS exhibited 100% reduction of bacteria. At the 50th laundering cycle, 0.3% of HTACC and 2.4% of COS indicated 100% bacterial reduction.

N-(2-hydroxypropyl)-3-trimethylammonium chitosan-poly(ɛ-caprolactone) copolymers and their antibacterial activity

“…A very strong peak at around 3.2 ppm was observed, which confirms the presence of methyl groups in the quaternary ammonium side chains (Lim & Hudson, 2004). Several other peaks at ı: 2.8, 3.21 and 4.53 could be ascribed to protons in quaternized side chains, respectively (Kim, Choi, & Yoon, 1998;Seong et al, 2000). The signals in the spectrum for chitosan backbone and PCL side chains were maintained almost the same with exception of a small shift for H-2 (ı: 2.93) which originally positioned at ı: 3.1 (see Fig.…”

Quaternized chitosan particles as ion exchange supports for label-free DNA detection using PNA probe and MALDI-TOF mass spectrometry

“…In the case of MBzC particles, a weak signal of aromatic protons at 7.5 ppm confirmed the presence of the benzyl group. Peak assignments of all quaternized chitosan derivatives agree very well with published data previously reported (Sajomsang, Tantayanon, Tangpasuthadol, & Daly, 2009;Seong et al, 2000;Sieval et al, 1998).…”

“…HTACC was synthesized according to a modified method of Seong, Whang, and Ko (2000). Chitosan (∼5 g) was dissolved in 1%v/v acetic acid at ambient temperature.…”

Enhancing antibacterial activity of chitosan surface by heterogeneous quaternization

“…They are typically synthesized either by direct quaternization of the amino groups of chitosan using alkyl halides under alkaline conditions (Domard, Rinaudo, & Terrassin, 1986;Polnok, Borchard, Verhoef, Sarisuta, & Junginger, 2004), by reductive N-alkylation reaction of chitosan with aldehydes via Schiff's base intermediates followed by quaternization with methyl iodide (Muzzarelli & Tanfani, 1985;Sajomsang, Gonil, & Saesoo, 2009) or by reductive N-alkylation reaction of chitosan with quaternary ammonium-type aldehydes (Suzuki, Oda, Shinobu, Saimoto, & Shigemasa, 2000). Reaction of the amino groups of chitosan with glycidyltrimethylammonium chloride (GTMAC) has been introduced as an alternative for N-selective reaction under acidic and neutral conditions (Seong, Whang, & Ko, 2000;Sun, Du, Fan, Chen, & Yang, 2006). A recent review on the synthesis and applications of quaternized derivatives of chitosan have been available in published literatures (Mourya & Inamdar, 2009;Sajomsang, 2010).…”