Sythesis Of N-halamines Based On S-triazine And Study On Antibacterial Finishing For Cotton Fabrics

To increase the additional value and expand the application of textiles, functional finishing of textile has been the hotspot in recent years. The devlopment of textile finishing is required to be enviromental, energy-saving and emission-reduction, and efficient. Therefore, multi-functional textile, and functional finishing and dyeing in one step emerge because of demand.There is a lot of microorganism existed in the nature, and its harm to human have become more and more serious, which leads to the increase of safety consciousness of people and rapid development of antimacrobial materials, especially in the textiles. Lots of different kinds of antimicrobial agent, such as quaternary ammonium salt, chitosan, metal and metal oxide, biguanide and N-halamine, have been appeared in the world. Among these compounds, N-halamine has attracted much attetion because of its effcicent, stable and rechargeble antibacterial properties. In the previous researches, the antibacterial textiles with N-halamine was prepared by pad-dry-curing precess and linking agent, which wasted amount of resource and energy, and seriously effected the physical and mechanical properties of textiles, especially breaking strength. The much loss of breaking strength has disadvantage of textile dressing and using. To solve this problem, a kind of reactive N-halamine precursor with cyanuric chloride was synthesized and applied to cotton fabric under low temperature to produce efficient and stable antibacterial textiles, which perfectly reserves the intrinsic properties of textile, such as breaking strength.The content of this thesis contains two parts. One is the design and synthesis of a series of N-halamine precursors based on s-triazine according to the stepwise improvement of antibacterial efficacy, stability and the development of enviromental textile finishing. These compounds are characterized by H-NMR, FT-IR and UV/vis spectra, and then applied to cotton fabrics with reactive dyeing process. The antibacterial properties, washing stability, UV stability, storage stability, and breaking strength of treated fabrics after chlorination are measured. The other is the synthesis, characrization and application of antibacterial reactive with N-halamine precursor. The antibacterial properties, dyeing properties and dyeing fastness are measured. And the effect of chlorinated condition on chlorine content and color properties is investigated.The background and significancy of this thesis is discribed in the first section. The advantage and disadvantage of different antimicrobial agents are introduced roughly, and a detailed introduction for the development of N-halamine in recent years in textile and other fields is discribed.In the two chapter the research work is about the synthesis of a novel dichloro-s-triazine-based N-halamine precursor, 2,2,6,6-tetramethyl-4-piperidinol-s-trizine(TMPT), and the preparation of antibacterial cotton fabrics. TMPT is characterized by 1H-NMR, FT-IR and UV/vis spectra. The compound is applied to cotton fabrics with reactive dyeing process under low temperature. The treated fabrics are chlorinted by dilute bleaching solution, and the optimum finishing condition is obtained as follows: 100 g/L Na2SO4, 1 g/L Na OH, 40%(owf) TMPT, 30℃, 3 h. The antibacterial fabrics prepared by reactive dyeing process have good retention rate of breaking strength and storage stability. However, the antibacterial fabrics show poor biocidal efficacy, and only 3~4 logs of S. aureus and E. coli O157:H7 can be inactivated within 30 min. The chlorine loading in the fabrics has some degree of decrease under washing conditon, and most of lost chlorine loading can not be recharged after washing.To increase the antibacterial properties and washing stability, a kind of monochloro-s-triazine-based N-halamine precursor,(4-(2,2,6,6-tetramethyl-4-piperidinol)-6-chloro-1,3,5-triazinylamino)-benzenesulfonat e(BTMPT), is synthesized based on TMPT after introduing water soluble group, sodium sulfanilate, in the three chapter. And to compare the difference of amide and amine in the biocide properties and stability, another monochloro-s-triazine-based N-halamine precursor(BTDMH) containing amide group is prepared. Compared to TMPT treated fabrics, the antibacterial fabrics prepared with BTMPT and BTDMH have better biocidal efficacy and washing stability. 6~7 logs of S. aureus and E. coli O157:H7 can be inactivated within short time and almost all of the reactive chlorine lost can be recovered after washing by exposing to dilute bleaching solution.. Besides, BTDMH treated has better biocidal efficacy, and worse washing and storage stability than BTMPT because of the exist of amide N-halamine.There is a lot of neutral salt used in the textile finishing with s-triazine derivatives, which increase the cost of production and can cause enviromental problem. To decrease the amount of neutral salt, a novel kind of s-triazine-based quaternarized N-halamine precursor is synthesized and the antibacterial cotton fabrics are prepared by reactive dyeing precess. Over 0.2% of chloring loading can be achieved without the exist of neutral salt, and 6 logs of S. aureus and E. coli O157:H7 can be inactivated within 1 min and 5 min, respectively. The antibacterial fabrics have good washing and storage stability. About 40% and 54% of reactive chlorine can be maintained after 50 washing cycles and 30 days storage, respectively. And the lost chlorine can be recovered after rechlorination.To accomplish one-step dyeing and functional finishing, and decrease the waste of resource and enviromental pollution, a kind of antibacterial reactive dye containing N-halamine precursor is synthesized in the fifth chapter. The antibacterial dyeing cotton fabrics are prepared by dyeing process and chlorinated by dilute bleaching solution. The chlorination condition has a big effect on the chlorine loading and color. With the decrease of p H, the chlorine loading becomes higher, but color fade is more and more serious. When p H of chlorination reached at 11, the chlorine loading in the fabrics is 0.12%, and the color difference is 2.7, compared with the unchlorinated samples. The chlorinated samples at p H 11 show perfect antibacterial properties, and 6 logs of logs of S. aureus and E. coli O157:H7 can be inactivated within 10 min and 5 min, respectively. The dyeing properties and fastness between reactive yellow X-R and antibacterial reactive dye are measured. Higher exhaustion and fixation rate can be obtained for the antibacterial reactive dye. Besides, the antibacterial reactive dye has good dyeing fastness as well as reactive yellow X-R.