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含全氟烷基抗菌剂的合成及其应用

Synthesis and Applications of the Perfluoroalkyl-containing Antimicrobial Compounds

【作者】 邵徽

【导师】 卿凤翎;

【作者基本信息】 东华大学 , 纺织化学与染整工程, 2004, 硕士

【摘要】 随着人们生活水平的不断提高和科学技术的发展,人们对自身的卫生保健意识日益增强。在致病菌的传播过程中,纺织品是一个重要的媒介,所以具有抗菌性能的织物正日益受到消费者的青睐。至今,种类众多的抗菌剂已被用来赋予织物抗菌性能。其中,季铵盐类表面活性剂因广谱的抗菌性能已广泛地应用于织物的抗菌整理。 但有时织物仅仅具有抗菌性能并不能确保穿着者的安全。例如为了保护病人和医护人员不被感染性的血液或体液传染,许多医用纺织品不仅要求具有良好的抗菌性能,同时要求有优良的拒血拒液等功能。战士用的军服同样有上述的要求。迄今,含全氟烷基化合物在织物的拒水拒油防污整理方面的应用非常广泛,不仅能显著降低织物的临界表面能,而且能保持整理后织物的透气性。 为制备一种能同时赋予织物抗菌和拒水拒油性能的多功能织物整理剂,我们首先设计并合成了新型的含全氟烷基和二烯丙基的季铵盐(PFDA)。PFDA的合成路线如Schemel所示。随后测定了PFDA的抗菌活性,PFDA对大肠杆菌8099(革兰氏阴性菌)和金黄色葡萄球菌ATCC 6538(革兰氏阳性菌)的最低抑菌浓度(MIC)均为7.8μg/ml。二烯丙基的引入使得PFDA能方便地作为阳离子聚合物单体用于均聚或共聚。于是我们通过乳液聚合得到PFDA与其他单体的共聚物乳液,并将其用于棉织物的整理。整理后的织物对大肠杆菌8099和金黄色葡萄球菌ATCC 6538的抑菌率分别达到99.9%和92.4%,拒油达到四级,但拒水效果不佳。 为了提高整理效果的耐久性,我们设计并合成了另一新型含氟烷基季按盐(p「sc),并在P「sC分子中引入硅氧偶联基团。pFsc的合成路线如S。lleme2所示。实验表明,经pFsc整理后的棉织物显示出耐久的抗菌活性和极低的临界表面能。经检测,整理后织物对金黄色葡萄球菌ATCC 6538的抑菌率达到97.3%,即使经过十次水洗后,抑菌率仍然大于95%。拒水拒油性能均达到5级,十次水洗之后也能达到4级。通过接触角测量的方法,我们估算出整理后的棉织物临界表面能为丫。=20士1 mN/m,远低于人体血液的42士2mN/m。CFs(CFZ)71+SChemeZ尹\/OH一二{竺逻竺~eo3(e:2丫卜办。日暨些二竺生e:3(e:2片人,洲八O。 l}Jones oxldation agent一(一)扮。~、/ Ho(cH:)3N(CH公2‘峡一 PTSAe:3(e:2丫~义。日c:3(eoZ丫、义。~仑品介丫\51(oM·)3 fPFSCPFSC O lO一51 l O/\与/产\ 2尹!.N尸\甲八+、 O。义V入(。:2)7。:3SUbstrate

【Abstract】 As the ever-growing demand for healthy living, there is a keen interest in materials capable of killing harmful microorganisms. Textile materials are suitable media for growing microorganisms. In the last few decades, the prevention of microbial attack on textile and wearers of textile materials has become increasingly important to consumers and textile producers. So far, various antimicrobial agents have been applied to impart antimicrobial properties to textile. Among them, the quaternary ammonium salts are widely used in antimicrobial finishing of textile.However, the antimicrobial materials would not essentially mean ensured safety of us. For example, to protect patients and the surgical team from infectious blood and other body fluids, some medical materials should possess not only antimicrobial properties but also blood repellency properties. The same is in the case of battle suits. To provide the treated surface with a low critical surface tension, fluorochemicals are most abundantly used for their ability to lower the critical surface tension of the treated surface well below that of most ’fluid other than a fluorocarbon.In the light of the facts above mentioned, we first designed and synthesized a novel quaternary ammonium salt (PFDA), which contains both perfluoroalkyl and diallyl groups. PFDA was designed to be a multifunctional textile finishing agent capable of providing fabrics with barriers against microorganisms, water, oil, soil and blood. The synthesis of PFDA was outlined in Scheme 1. Consequently, the antimicrobial activities of compound PFDA were tested against Escherichia coli 8099 as a Gram-negative strain and Staphylococcus aureus ATCC 6538 as a Gram-positive strain. Both the minimum inhibitory concentration(MIC) values were 7.8 μ g/ml. Moreover, diallyl groups were innovatively introduced into the target molecular, which made itself a good monomer for polymerization. By emulsion copolymerization, we applied PFDA as one of monomers to give the copolymeric emulsion, which was used to treat the cotton fabrics by the pad-dry-cure method. The treated fabrics showed good antibacterial properties. The killing bacterial fates against E. coli 8099 and S. aureus ATCC 6538 were 99.9% and 92.4%, respectively. At the same time, the treated fabrics also showed good oil repellency but little waterproof property.To obtain more accessible application and durable effect, another novel quaternary ammonium salt (PFSC) was designed and synthesized. The 3-(trimethoxysilyl)propyl group introduced into the molecule can bind to many material surfaces. That improved the durability of the treated materials as well as its scope of applications. The synthesis of PFSC was outlined in Scheme 2. PFSC was applied as a surface modification agent to provide the treated cotton fabrics with the durable antimicrobial activity and low critical surface energy simultaneously. The treated fabrics showed a 97.3 % killing bacterial rate against S. aureus ATCC 6538. Even after 10 laundering cycles, the antimicrobial activities of treated specimens still remained at a high level, reaching at 95.6%. The treated specimen also showed the super-low critical surface energy γc=20± l mN/m, which is markedly lower than 42+2 mN/m of man-made blood.

  • 【网络出版投稿人】 东华大学
  • 【网络出版年期】2004年 03期
  • 【分类号】TS195.2
  • 【被引频次】3
  • 【下载频次】290
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