Synthesis and characterization of metal‐containing polyurethanes with antibacterial activity

Metal salts of mono(hydroxypentyl)phthalate [M(HPP)₂, where M is Ca²⁺, Cd²⁺, Pb²⁺, or Zn²⁺] were synthesized by the reaction of 1,5‐pentane diol, phthalic anhydride, and metal acetate. A new series of metal‐containing polyurethanes containing ionic links in the main chain were synthesized by the reaction of hexamethylene diisocyanate or toluylene 2,4‐diisocyanate with the M(HPP)₂ salts. The structures of the monomers and polymers were confirmed with infrared, ¹H‐NMR, and ¹³C‐NMR spectra and elemental analysis. The polymers were also characterized with thermogravimetric analysis, differential scanning calorimetry, and solubility and viscosity measurements. The antibacterial activity of these polyurethanes was investigated with the agar diffusion method. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 85: 1194–1206, 2002     

Preparation of water‐soluble chitosan derivatives and their antibacterial activity

Carboxymethyl chitosan sodium (CMCTS) was synthesized by chitosan and chloroacetic acid under an alkali catalyst. Acrylic acid sodium salt and methylacrylic acid sodium salt were grafted onto CMCTS to obtain copolymers with good water solubility. The graft reaction was carried out at 70°C for 2 h, and ammonium persulfate was used as an initiator. The structure changes of chitosan and its derivatives were investigated by the FTIR. The antibacterial activity of chitosan derivatives against Staphylococcus aureus and Escherichia coli were explored by the viable cell counting method. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 85: 1357–1361, 2002     

新型吡唑啉衍生物合成与抑菌活性实验研究

根据α,β-不饱和醛酮亲核加成反应原理合成化合物L{[3-(4-N,N-dimethyl-pyenyl)-5-Anthracen-9-yl]-Pyrazoline}和化合物M[3-ferroceny-5-(Anthracen-9-yl)-Pyrazoline]。利用~1H NMR和~(13)C NMR对化合物进行结构表征,通过抑菌实验研究化合物抑菌生物活性。探析新型吡唑啉衍生物对革兰氏阳性菌、革兰氏阴性菌和真菌的抑菌效果,研究其结构变化对活性的影响。结果表明,化合物L和M对典型革兰氏阳性菌和典型革兰氏阴性菌有一定的抑菌效果,对真核细胞型微生物作用不明显。通过比较两者对细菌的作用结果(抑菌圈直径的大小),化合物L的抑菌作用明显强于化合物M,化合物L吡唑啉环连接N、N-二甲基苯环可能增强了抑菌生物活性。     

新型壳聚糖季铵盐抗菌剂的合成及其性能

先用两步法合成了无O-甲基化 N,N,N-三甲基壳聚糖季铵盐（TMC）,再通过相转移催化合成了N,N,N-三甲基O-辛基壳聚糖季铵盐（TMOC）,用 FTIR、1H NMR、EA、TG 等方法对产物进行表征,并研究其抗菌性能。结果表明,TMOC在pH值为5.5的抗菌活性优于pH值为7.2的抗菌活性;TMOC对革兰阳性菌S. aureus的抗菌活性比革兰阴性菌E. coli强。在不影响水溶性的前提下,O-烷基化改性能有效提高壳聚糖季铵盐的抗菌活性,并且抗菌活性随着O-烷基化度的提高而提高。研究结果为壳聚糖基抗菌剂的改性和制备提供了依据。     

硫脲与碘化钆配合物的合成、表征及抗菌活性研究

报道了配合物GdI3.2CS(NH2)2.10H2O的新合成方法,通过元素分析、X-射线粉末衍射、红外光谱、质谱、差热-热重分析,确定了配合物的组成和结构,首次测定了配体碘化钆、硫脲和配合物对枯草芽孢杆菌、葡萄球菌和大肠杆菌的抗菌活性。抗菌活性测试结果表明,所有试样对枯草芽孢杆菌的杀死作用显著,且高浓度溶液(0.05 mol/L)比低浓度溶液(0.01 mol/L)的抗菌效果好;对金黄色葡萄球菌、大肠杆菌的杀死作用不明显;浓度为0.05 mol/L时,配合物GdI3.2CS(NH2)2.10H2O对枯草芽孢杆菌的杀死作用大于CS(NH2)2和GdI3.9H2O。     

N-吡啶取代喹诺酮衍生物的合成及抗菌活性

以2,4-二氯-5-氟苯乙酮为起始原料,通过β-酮酸酯化,与原甲酸三乙酯缩合,同2-氨基吡啶发生取代,再经环合反应、硼配合反应和哌嗪化反应合成得到了N-吡啶取代喹诺酮抗菌化合物,总收率为39．3％,并对其抗菌活性进行了试验。     

双二茂铁基希夫碱的合成及抗菌活性

利用二茂铁甲醛分别与1,2-乙二胺、1,3-丙二胺和1,4-丁二胺缩合,合成了3种双二茂铁基希夫碱,进行了生物活性实验。结果表明,3种双二茂铁基希夫碱对大肠埃希氏菌和金黄色葡萄球菌均具有较好的抗菌活性,1,3-丙二胺双缩二茂铁甲醛对金黄色葡萄球菌的抑菌能力最强,生物效价为210 U/mg（与四环素盐酸盐相比较）;1,4-丁二胺双缩二茂铁甲醛对大肠埃希氏菌的抑菌能力最好,生物效价为1 058 U/mg（与四环素盐酸盐相比较）。3种双二茂铁基希夫碱对大肠埃希氏菌的抑菌能力比对金黄色葡萄球菌的抑菌能力强。     

Polymers from renewable resources: XIX: Synthesis and characterization of copolymers from cardanyl acrylate and vinyl monomers

A large number of copolymers have been prepared from cardanyl acrylate on suspension polymerisation with vinyl monomers like methyl acrylate, ethyl acrylate, butyl acrylate, etc. These copolymer beads are almost uniform in size. Infrared spectral and swelling behaviour studies explain their various characteristics. The thermal behaviour of the copolymer beads has been studied with the help of a new computer method known as the LOTUS package method.     

富马酸单己酯的合成及其抑菌活性

以马来酸酐和正己醇为原料,无水AlCl3为异构化催化剂,合成了标题化合物。用正交试验法优化了合成反应条件:醇解时间160 min,醇解温度60℃,异构化时间190 min,异构化温度105℃和AlCl3用量2.5 g/mol酸酐,在优化条件下富马酸单己酯收率81%。抑菌活性测试结果表明,在给药量为5 mg/mL时,标题化合物对大肠杆菌、枯草芽孢杆菌和苏云金杆菌均有较好的抑菌活性。     

稀土-蛋氨酸-邻菲咯啉配合物的合成、表征及抗菌活性研究

采用冷凝回流法合成了4种新型稀土(镧、铕、钐和钕)-蛋氨酸-邻菲咯啉三元配合物,通过元素分析、EDTA-滴定、摩尔电导、红外光谱,确定了配合物的组成为RE(Met)_3phenCl_3·3H_2O(RE:La~(3+)、Eu~(3+)、Sm~(3+)、Nd~(3+);Met=L-蛋氨酸;phen=邻菲咯啉).抗菌活性的研究表明,与配体相比,稀土三元配合物对大肠杆菌(Escherichia coli)和金黄色葡萄球菌(Staphylococcus aureus)均具有更强的抑菌能力.     

新型芳腙基噻唑衍生物的合成及抗菌活性研究

以取代苯甲醛与氨基硫脲为原料合成了11种芳基噻唑衍生物,经IR、1HNMR、MS及元素分析确定了化合物的结构,并分别测试了这些化合物对8种革兰氏阳性、阴性菌和3种真菌的抑菌活性。     

稀土三元配合物的合成、表征及其抗菌活性研究

以稀土氯化物、联咪唑和噻吩甲酰三氟丙酮为原料制备了一系列新型稀土三元配合物Ln(TTA)3L(Ln=Nd3+,Eu3+,Er3+;TTA=噻吩甲酰三氟丙酮;L=联咪唑),抗菌实验结果显示,三元配合物抑菌圈直径为12～17 mm,对大肠杆菌、金黄色葡萄球菌具有一定的抑制作用,且对大肠杆菌的抑制效果较好。     

对氟苯甲醛缩乙醇胺席夫碱合成、表征及抑菌活性的测试

通过对氟苯甲醛与乙醇胺的反应，合成了对氟苯甲醛缩乙醇胺席夫碱，并对其进行了元素分析、核磁共振氢谱、红外光谱、紫外光谱表征。抑菌实验表明，该席夫碱对金黄色葡萄球菌和革兰氏阴性菌均有较好的抑制作用。     

稀土三元配合物的合成、表征及其生物活性研究

以氯化镧、席夫碱、邻菲啰啉为原料,制备了新型稀土镧三元配合物,通过元素分析、紫外光谱、红外光谱、透射电子显微镜等手段对其进行了表征,确定了三元配合物的化学组成为La(L)phen(NO3)3C2H5OH.CH3OH。抗菌实验结果表明,配合物对大肠杆菌和金黄色葡萄球菌的抑菌圈直径分别为26 mm和20 mm,最小抑菌浓度分别为60 mg/L和130 mg/L,具有较强的抑制作用,且对大肠杆菌的抑制效果较强。     

含4-噻唑啉酮环的新金刚烷类化合物的合成及抗癌活性研究

以1-金刚烷甲酸为原料,通过酯化、肼解制得1-金刚烷甲酰肼,1-金刚烷甲酰肼再与芳香醛反应得到相应的酰腙,最后以苯和DMF为溶剂,酰腙与巯基乙酸脱水环化成2-芳基-3-(1-金刚烷甲酰胺基)-4-噻唑啉酮类化合物,并利用IR、1HNMR、13CNMR、ESI-MS和元素分析对7个目标化合物的结构进行了表征。用MTT方法评价了它们在体外对HepG-2,A549-1和231-2 3种癌细胞株的体外生长抑制活性。结果表明,所合成的7个新化合物均具有潜在的体外抑制癌细胞生长活性。     

芳香醛(酮)缩氨基硫脲的微波合成及其抗菌活性的研究

肼基二硫代甲酸甲酯与相应的醛或酮在微波辐射下经2~3.5 min反应,得到3-二取代甲(乙)撑肼基二硫代甲酸甲酯,产率91%~96%。再与胺在微波辐射下经35~45 min反应,得到目标化合物,产率80%~90%。合成的6个目标化合物通过熔点测定和质谱、红外光谱、核磁共振氢谱分析,对其结构进行确证,并测试了化合物的抑菌活性。     

Preparation,characterization, and antibacterial activity of cationic nanopolystyrenes

Cationic nanopolystyrenes (CNPSs) were prepared by the polymerization of styrene with a cationic polymerizable emulsifier, N-(2-(methacryloyloxy)ethyl)-N,N-dimethyltetradecane-1-ammonium bromide (MDTB), in the presence of 2,2′-azobis(2-methylpropionamidine) dihydrochloride (APPH). The polymerization kinetics was investigated through monomer conversion versus polymerization time. ¹H NMR spectra and FTIR spectra were used to confirm the structures of MDTB and nanopolymers. The particle size, ζ-potential, molecular weight, and thermal stability were also investigated by Zetasizer, gel permeation chromatography, and thermogravimetric analysis, respectively. The antibacterial activities of the obtained products were evaluated by minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) against Staphylococcus aureus ATCC 29913 (S. aureus, a Gram-positive bacterium) and Escherichia coli ATCC 25922 (E. coli, a Gram-negative bacterium). The results indicated that the polymerization has the characteristics of microemulsion polymerization, all nanopolystyrenes are cationic and can be stored in the form of a microemulsion in aqueous phase, CNPSs present stable chemical structure at 190 °C, and their MIC and MBC reach 0.0625 and 0.125 mg mL⁻¹ for E. coli, 0.0325 and 0.0625 mg mL⁻¹ for S. aureus, respectively. Therefore, CNPSs are a promising new type of polymer antimicrobial agent, which can be used in the development of antimicrobial polymer materials and their products. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020 , 137, 48405.     

Synthesis and characterization of silicon-containing graft copolymers

Poly(4-t-butoxycarbonyloxystyrene)-g-poly(dimethylsiloxane) and poly(t-butylmethacrylate)-g-poly(dimethylsiloxane) with various chemical compositions were synthesized via free radical polymerization of 4-t-butoxycarbonyloxystyrene (TBCS) or t-butylmethacrylate (TBMA) with silicone macromers. These macromers were prepared by anionic ring-opening polymerization of hexamethylcyclotrisiloxane (D₃) and subsequent termination with a chlorosilane compound having a methacrylate functionality. The morphology of the graft copolymer systems was investigated by DSC and TEM.     

Synthesis of phosphonated styrenic copolymers and their chemical modifications

We report, for the first time, the synthesis of a phosphonated styrenic monomer dimethyl vinylbenzyl phosphonate (VBP) according to the methods described in the literature for its equivalent diethyl vinylbenzyl phosphonate, and also the monodealkylation of this monomer (VBP) to the monosalt in a neutral medium and to the corresponding monoacid via a sulfonic resin. Various statistical copolymers and statistical block copolymers of styrene and VBP were prepared with different molar percentages of these comonomers. The dealkylation of statistical copolymers was carried out in the same way as for VBP. The phosphonated statistical copolymers, prepared, were characterized by various analytical methods which show good agreement with their structures. © 2002 Society of Chemical Industry