Preparation of silicone containing 2,2,6,6-tetramethyl-4-piperidinol-based N-chloramine for antibacterial polyethylene via interpenetration in supercritical carbon dioxide

Functionalization of polyethylene (PE) with powerful biocides through a friendly and efficient procedure is necessary to obtain extended applications. A novel CO₂-philic 2,2,6,6-tetramethyl-4-piperidinol (TMP)-based N-chloramine silicone was synthesized via Pt-catalyzed silane alcoholysis between the Si H of poly(methylhydrosiloxane) and O H of TMP and followed by chlorination of amine N H originating from TMP to N Cl. The TMP-based N-chloramine silicone was interpenetrated into PE using supercritical carbon dioxide (scCO₂) as working solvent. It was shown that the thickness of the TMP-based N-chloramine silicone layer on PE can be easily controlled by the interpenetration pressure, reaching a maximum value of 70 nm at 28 mp. The synthetic procedures and the interpenetration results were characterized by Fourier transform infrared, scanning electron microscopy, and X-ray photoelectron spectroscopy. In contrast with pristine PE that did not show biocidal ability, the TMP-based N-chloramine silicone modified PE imparted powerful antibacterial abilities, exerting total kills of both Staphylococcus aureus and Escherichia coli of ~10⁷ cfu mL⁻¹ in 30 min. The biocidal functionality was durable toward washings, storage, and ultraviolet exposure and the recoverability of lost chlorines was good. The interpenetration in scCO₂ tactic provides an environmentally friendly and universal approach to functionalize inert substrates due to no needs of harmful solvent and chemical linkages with biocides. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136, 47614.     

羧甲基壳聚糖季铵盐的制备及其抑菌性能研究

以不同分子量的壳聚糖为原料合成了一种新型水溶性O-羧甲基-N-三甲基壳聚糖季铵盐(CMTMC),用FTIR表征了其结构,同时进行了抑菌实验.结果表明在水介质中CMTMC对大肠杆菌、金黄色葡萄球菌和枯草芽孢杆菌的最低抑菌浓度分别为1 μg·mL-1、1 μg·mL-1和2 μg·mL-1,在0.5%醋酸溶液介质中的抑菌效果比在水介质中更好.     

Preparation of O‐diallylammonium chitosan with antibacterial activity and cytocompatibility

In this study, a derivative of chitosan, O‐hydroxy‐2,3‐propyl‐N‐methyl‐N,N‐diallylammonium chitosan methyl sulfate (O‐MDAACS), was synthesized by reacting chitosan with methyl diallyl ammonium. The O‐MDAACS was confirmed by Fourier transform infrared spectroscopy and ¹H NMR. Characterization was conducted including X‐ray diffraction, differential scanning calorimetry and thermogravimetry. The antibacterial activities of O‐MDAACS against Staphylococcus aureus and Klebsiella pneumoniae were evaluated. The minimum inhibitory concentrations on O‐MDAACS were 3.7% and 23% of those on chitosan against S. aureus and K. pneumonia, respectively. The minimum bactericidal concentrations on O‐MDAACS were 7% and 36% of those on chitosan against S. aureus and K. pneumonia, respectively. Thus the antibacterial activity of O‐MDAACS was higher than that of chitosan. The cytocompatibility was evaluated in vitro with L929 fibroblasts. The results showed that after 72 h incubation the cell viability on O‐MDAACS was about 12% and 59% higher than those on chitosan and on control, respectively. © 2012 Society of Chemical Industry     

季铵盐型抗菌树脂合成及其漆膜的抗菌性能

采用聚合反应合成了一种季铵盐型抗菌树脂,通过漆膜的抑菌圈测试、抗菌率测试以及模拟不同环境对漆膜抗菌效果的影响测试对抗菌树脂的抗菌性能进行了评价,并考察了抗菌树脂漆膜的力学性能。结果表明:季铵盐抗菌剂的含量为6%时,漆膜对金黄色葡萄球菌及大肠杆菌的抗菌率均能达到99%以上。在此含量下,对漆膜的力学性能影响不大,且漆膜具有良好的抵抗恶劣环境的能力,漆膜被擦拭1000次后,其抗菌率仍能达到95%以上,具有良好的抗菌持效性能。     

季铵盐型洗手液的制备及其抗菌性能研究

通过对原料的选择和配方的优化,制备了一种季铵盐型抗菌洗手液。该洗手液配方(以质量分数计)由0.75%十二烷基聚氧乙烯醚硫酸钠(AES),2.25%十四烷基甲基二羟乙基溴化铵(TMDAB),20%椰油酰胺丙基甜菜碱(CAB-35),0.25%醇醚磺基琥珀酸单酯二钠盐(MES),1.5%椰子油二乙醇酰胺(6501),1%甘油,0.1%二羟甲基海因(DMDMH),少量香精及色素,少量柠檬酸调p H和余量的蒸馏水组成。经过测试表明该洗手液对大肠杆菌和金黄色葡萄球菌的杀菌率达到99.99%和100%,产品稳定性、起泡性好,生产成本较低,与市售的某些抗菌洗手液相比,该洗手液显示出一定的优越性。     

O-一氯均三嗪-N,N,N-三甲基壳聚糖的合成及其在羊毛织物抗菌中的应用

采用甲醛甲酸法合成N,N,N-三甲基壳聚糖（TMC）,再用三氯均三嗪与TMC反应,合成带有可与纤维反应的水溶性O-一氯均三嗪-N,N,N-三甲基壳聚糖（MCT-TMC）。采用FTIR、XRD、热重和元素分析等对产物进行表征,并测试其抗菌性能。将产物对羊毛织物进行抗菌整理,研究整理时间和浓度等工艺条件对抗菌性能的影响。结果表明,TMC和MCT-TMC具有较好的抗菌性能;将其用于羊毛织物抗菌整理的最佳工艺条件为：整理时间60min,整理浓度分别为3%（owf）和2%（owf）;经TMC整理的织物对E.coli和S.aureus的抑菌率分别为97.8%和99.2%,MCT-TMC整理的织物对E.coli和S.aureus的抑菌率分别为98.6%和99.8%。MCT-TMC整理羊毛织物的耐洗涤性能比TMC有显著提高,洗涤后抑菌率仍达到90%以上。     

Preparation and characterization of quaternary bacterial cellulose composites for antimicrobial oil-absorbing materials

The treatment of various types of oily wastewater is paramount for environmental protection. Bacterial cellulose (BC) stands out as a highly promising material for oil/water separation, owing to its exceptional mechanical properties and three-dimensional porous structures. However, excessive hydroxyl groups on BC make it highly hydrophilic, reducing oil absorption and promoting bacterial growth, affecting its stability. To address these challenges, we developed a straightforward in situ polymerization method for the preparation of BC-DMC composites. The innovation lies in the concurrent enhancement of BC's hydrophobicity and antimicrobial properties only through the addition of 2-(Methacryloyloxy)ethyltrimethylammonium chloride (DMC), considerably simplifying the synthesis of materials possessing oil-absorbing and antimicrobial properties. Morphological and structural characterization results confirmed the successful combination of DMC onto BC while maintaining its porous structure. After process parameter optimization, the BC-DMC composites exhibited a remarkable increase in contact angle (117.7° compared with pure BC's 19.5°). It also demonstrated excellent oil absorption performance, with maximum capacities exceeding 30 g/g for different oils, maintaining values above 20 g/g even after eight cycles. In addition, the BC-DMC composites exhibited strong antibacterial activity, with rates of 82.4% against Escherichia coli and 97.5% against Staphylococcus aureus. The antibacterial mechanism of the BC-DMC composites was also discussed. Our novel BC-DMC composites provides excellent oil absorption and antibacterial properties, making it highly applicable in the field of oily wastewater treatment and serving as a valuable reference for other researchers.     

聚有机季铵盐织物抗菌柔软剂的合成与应用

以丙烯酸羟丙酯（HPAA）、烯丙基环氧聚醚（APE500）和十八叔胺（Q18）为原料,在引发剂偶氮二异丁腈（AIBN）作用下,进行溶液聚合,合成新型非有机硅类长链聚有机季铵盐（VPEQ18）。利用红外光谱对其进行表征,分析表明VPEQ18中含有与预期结构相同的基团,说明VPEQ18合成成功。利用柔软度仪、折皱弹性仪、全自动色差计对VPEQ18的应用性能进行研究,最终确定在棉布大小为6cm?0cm,含固量30%的VPEQ18乳液用量为3g/100g H2O,焙烘温度为180℃,焙烘时间为90s的工艺条件下,经VPEQ18整理的织物能够达到理想的柔软、顺弹、抗菌的效果。     

有机硅季铵盐的制备及其抗菌性能研究

利用三甲氧基硅烷(WD-930)与二甲基十八烷基烯丙基氯化铵(DAOAAC)进行反应,合成了阳离子抗菌剂[N,N-二甲基-N-十八烷基氨丙基三甲氧基硅烷氯化铵(DOATAC)]。以溴酚蓝为指示剂、二氯乙烷为分相溶剂,采用两相化学滴定法测定DOATAC的含量;用红外光谱(FT-IR)、元素分析和熔点测定仪等对DOATAC产物进行了理化分析;利用薄层色谱法,对所制备的阳离子抗菌剂的合成路线及其纯化过程进行跟踪;最后对产物的抗菌性能和耐洗性能进行测定。研究结果表明,当抗菌整理液中w(DOATAC)=0.06%时,经该整理液整理的棉布,对金黄色葡萄球菌和大肠杆菌的抑菌率均超过90%,并具有优良的抗菌耐洗性,洗涤50次后其抑菌率仍超过70%。     

季铵型改性壳聚糖的制备及其在兔毛织物抗菌整理中的应用

以三乙胺和环氧氯丙烷为原料,合成醚化剂3-氯-2-羟丙基三乙基氯化铵。以甲壳素为原料通过醚化反应合成了季铵型甲壳素（CCT）,再经脱乙酰得到季铵型阳离子改性壳聚糖（CCTS）。采用红外光谱（FTIR）、核磁碳谱（¹³C NMR）对其化学结构进行了表征,运用黏度法和分光光度法测定了黏均分子量和溶解性等理化性能。采用最小抑菌法对CCTS的抗菌活性进行了测定,得到其对大肠杆菌的最低有效抑菌浓度（MIC）为0.2g/L,优于天然壳聚糖的MIC值。以柠檬酸为交联剂、次磷酸钠为催化剂,用CCTS对兔毛织物进行抑菌整理,考察织物经整理的抑菌效果和耐洗性。经5次洗涤后结果表明,CCTS对大肠杆菌的抑菌率达99.9%以上,抑菌率高于CCT和天然壳聚糖,是一种针对动物毛织物良好的天然高分子长效抑菌整理剂。     

带有乙烯基苄基氯长链季铵盐的合成及抑菌性能研究

以对乙烯基卞基氯(C9H9Cl)为原料分别与二甲基十二烷基叔胺(12DMA)、二甲基十四烷基叔胺(14DMA)、二甲基十六烷基叔胺(16DMA)进行亲核取代反应合成C9H9Cl-12DMA、C9H9Cl-14DMA和C9H9Cl-16DMA 3种标题化合物,并用FT-IR、1HNMR、EA和TG等手段表征其结构。将3种新标题化合物采用抑菌圈法对大肠杆菌、金黄色葡萄球菌和枯草芽孢杆菌抑菌活性进行测试,结果表明杀菌活性大小顺序为:C9H9Cl-14DMAC9H9Cl-16DMAC9H9Cl-12DMA。     

Study on antibacterial behavior of insoluble quaternary ammonium

Insoluble crosslinked polystyrenes (PS) grafted with different quaternary ammonium groups were synthesized as antibacterial agents. Their antibacterial activities against Staphylococcus aureus were investigated by a colony count method. It was found that when the concentration of the insoluble antibacterial agent was low, the antibacterial activity was different from that of the typical soluble antibacterial agent. The antibacterial activity was bacteriostatic rather than bactericidal. A model for explanation of the antibacterial activity of the insoluble ammonium salt was set up. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci, 2006     

Synthesis and water absorbency of polyampholytic hydrogels with antibacterial activity

Amphoteric terpolymers of acrylic acid (AA), acrylamide (AM), and N,N′‐dimethyl‐N‐ethylmeth‐acryloxylethylammoniumbromide (DMAEA‐EB) with varied compositions P[AA‐AM‐(DMAEA‐EB)] were synthesized by inverse suspension polymerization. The components of P[AA‐AM‐(DMAEA‐EB)] were verified by FTIR spectroscopy. The water absorption ability and antibacterial activity of the copolymer against Escherichia coli(E. coli) and Staphylococcus hyicus(S. hyicus) suspended in sterilized physiological saline were investigated. The introduction of  N⁺R₄ may increase the water absorbency of P[AA‐AM‐(DMAEA‐EB)] in some degree because of the excellent hydrophilicity of  N⁺R₄. The AA‐AM‐(DMAEA‐EB) hydrogels exhibited high antibacterial activity against bacteria tested. The process of adsorption between live bacteria cells and resins was at least partially reversible. A peak of antibacterial efficiency existed with increasing contact time. The resin killed 96.6% E. coli organisms and 90.3% S. hyicus organisms, respectively, within 30 min of contact at dosage of 0.1g. The concentration of DMAEA‐EB has a special effect on the antibacterial activity of the polyampholytic hydrogels, which is different from polycation. It was observed that the antibacterial activity of the resin with 2 mol % of DMAEA‐EB is superior to the copolymers tested with other compositions. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

改性活性炭负载高分子季铵盐的杀菌性能

引言活性炭比表面积大、吸附性能好,广泛应用在空气污染防治和工业废水处理中,如大型通风系统的过滤器、肾透析病房的水处理系统[1-2]。然而,活性炭表面易繁殖细菌,使其本身也成了微生物的污染源,从而影响净化空气或水的效果[3]。目前,对抗菌炭材料的研究越来越受到关注,多数工作者     

Fabrication of superhydrophobic and antibacterial surface on cotton fabric by doped silica-based sols with nanoparticles of copper

The study discussed the synthesis of silica sol using the sol-gel method, doped with two different amounts of Cu nanoparticles. Cotton fabric samples were impregnated by the prepared sols and then dried and cured. To block hydroxyl groups, some samples were also treated with hexadecyltrimethoxysilane. The average particle size of colloidal silica nanoparticles were measured by the particle size analyzer. The morphology, roughness, and hydrophobic properties of the surface fabricated on cotton samples were analyzed and compared via the scanning electron microscopy, the transmission electron microscopy, the scanning probe microscopy, with static water contact angle (SWC), and water shedding angle measurements. Furthermore, the antibacterial efficiency of samples was quantitatively evaluated using AATCC 100 method. The addition of 0.5% (wt/wt) Cu into silica sol caused the silica nanoparticles to agglomerate in more grape-like clusters on cotton fabrics. Such fabricated surface revealed the highest value of SWC (155° for a 10-μl droplet) due to air trapping capability of its inclined structure. However, the presence of higher amounts of Cu nanoparticles (2% wt/wt) in silica sol resulted in the most slippery smooth surface on cotton fabrics. All fabricated surfaces containing Cu nanoparticles showed the perfect antibacterial activity against both of gram-negative and gram-positive bacteria.     

季铵型阳离子聚丙烯酰胺的无盐染色行为

以季铵型阳离子聚丙烯酰胺作为一种新的阳离子助剂对棉纤维进行处理,应用于活性染料无盐染色,对染色过程中染料与处理后棉纤维之间的吸附类型、吸附热力学及吸附动力学进行了研究。结果表明,无盐染色过程符合Langmuir吸附模型;吸附过程是放热自发进行的,低温有利于染料的吸附;吸附动力学符合二级动力学模型,属于化学吸附过程。与传统有盐染色结果相比,染色后的阳离子化棉纤维色深增加,染料利用率提高。     

深度共熔溶剂对桉木组分的溶解选择性

制备了不同季铵盐三丁基甲基氯化铵(MTBAC)、四甲基氯化铵(TMAC)、苄基三乙基氯化铵(TEBA)和氯化胆碱(ChCl)分别与DL-乳酸(HL)以摩尔比1:9合成的深度共熔溶剂,并将用于溶解桉木粉中木质素。结果表明,由苄基三乙基氯化铵/DL-乳酸(TEBA/HL)合成的深度共熔溶剂处理桉木粉,在90 ℃下反应10 h,木质素溶解率达92.3wt%,综纤维素溶解率仅为8.3wt%;同时,木质素与综纤维素溶解选择性系数之比K达到158.5,表明TEBA/HL对木质素的溶解选择性最佳。通过红外光谱(FT-IR)分析各分离产物,证明提取物中有木质素特征官能团。通过凝胶渗透色谱(GPC)分析表明分离产物相对分子质量均有所降低。通过固体13C核磁共振谱(CP/MAS 13C NMR)分析90 ℃下TEBA/HL中分离产物结构,证明其结构征符合阔叶材木质素结构特点。     

含酯基双子表面活性剂的合成

以长碳链烷基酸与2-二甲氨基乙醇、盐酸、环氧氯丙烷为原料,通过3步反应合成了3种季铵盐阳离子双子表面活性剂。正交试验确定合成目标产物的最佳反应条件为:中间体N-(3-氯-2-羟丙基)-N,N-二甲基月桂酸乙基氯化铵与二甲基脂肪酸乙基叔胺的物质的量比为1∶1.1,100℃下反应12h。3种目标产物结构均通过IR、1HNMR得到证实。     

糖苷基季铵盐与α-烯基磺酸钠复配体系的表面活性

研究了糖苷基季铵盐(CAPG)与α-烯基磺酸钠(AOS)复配体系的稳定性以及在表面和溶液中的相互作用.结果 表明,复配体系具有很好的稳定性,在形成胶束的能力、降低表面张力的效能及效率方面均有显著的提高,当n(CAPG):n(AOS)=1:1时增效作用最为明显,其cmcT(临界胶束浓度)、γcmc(临界胶束浓度时的表面张力)和cπ:柏(表面张力为40 mN·m-1时表面活性剂的总浓度)分别为4.4×10-5mol·L-1,24.9 mN·m-1和1.7×10-5mol·L-1,混合表面活性剂在表面和胶束中的相互作用参数βσ和βm分别为-15.93和-14.29,表现出很好的协同效应.     

高岭石-季铵盐插层复合物脱嵌反应热动力学

以张家口高岭土为原料,采用多次置换插层的方法制备了高岭石-季铵盐插层复合物.XRD分析表明十二烷基三甲基氯化铵分子进入高岭石层间,并使其层间距d001扩大至3.50 nm.利用TG、DSC分析数据对高岭石-季铵盐插层复合物的热分解行为进行了动力学研究.结果表明复合物在加热过程中发生两步反应,第一步是插层剂分子于200.50℃发生脱嵌反应,第二步为高岭石于518.88℃发生脱羟基反应.针对第一阶段的脱嵌反应,采用“特征点分析法”进行了动力学研究,并计算得到了活化能E =218.327 kJ/mol,指前因子A=2.392×1022 s-1,机理函数为f(α)=2×(1-α)3/2.