新型高分子抗菌剂的合成与性能研究
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摘要
高分子抗菌剂由于其高效杀菌、杀菌时效性长等优点,日益受到人们的广泛关注。目前研究和使用的高分子抗菌剂主要有季铵盐类、季膦盐类、吡啶盐类、有机锡类和胍盐类,它们都具有一定地杀菌效果,但是普遍存在热稳性和加工性差的问题,限制了其在工业上的大规模应用。基于此种情况,本论文设计合成了新型咪唑盐类高分子抗菌剂,咪唑盐独特的五元环结构可使此类抗菌剂具有很高的热稳定性。
本论文首先通过研究抗菌剂的结构与其热稳定性间的关系,发现咪唑盐类高分子抗菌剂尤其是经BF4和PF6离子取代后的抗菌剂具有很好的热稳定性,初始热分解温度高达350 oC,能够满足大部分加工、应用的要求。其次考察了咪唑盐类高分子抗菌剂的结构与其抗菌性能的关系,结果表明:咪唑盐上取代的疏水碳链长度以及不同阴离子种类对抗菌效果有较大的影响。当咪唑盐上取代的疏水碳链长度为12时,抗菌效果最好,过长或过短都会减弱其抗菌能力(其中3-十二烷基-1-乙烯基咪唑溴盐聚合物对大肠杆菌的最小抑菌浓度(MIC)仅为33μg/mL,对金黄色葡萄球菌的MIC值为47μg/mL);不同阴离子种类抗菌剂的抗菌活性顺序为Br>BF4>PF6。
本文还将咪唑盐类高分子抗菌剂应用到高分子抗菌药物这一前沿领域。模仿抗菌多肽的结构,将抗菌剂与亲水的聚乙二醇大分子单体共聚合成了三种阳离子型双亲性共聚合物:PEG-co -3-丁基-1-乙烯基咪唑溴盐聚合物(PEG-co-3- P[BVIM][Br])、PEG-co -3-己基-1-乙烯基咪唑溴盐聚合物(PEG-co-3-P[HVIM][Br]),和PEG-co-3-十二烷基-1-乙烯基咪唑溴盐聚合物(PEG-co-3-P[DDVIM][Br])。并研究了共聚物结构,及其与血液相容性和抗菌性能的关系。结果发现咪唑盐两亲性阳离子聚合物在水中自装成纳米颗粒,纳米颗粒的粒径随疏水烷基链长的变短而变小, PEG-co-3-P[BVIM][Br]、PEG-co-3-P[HVIM][Br]和PEG-co-3-P[DDVIM][Br]形成的纳米颗粒的体积平均粒径分别为88 nm、72 nm和19 nm;抗菌共聚物的溶血性随咪唑盐上取代烷基长度的缩短而减弱。PEG-co-3-P[DDVIM][Br]、PEG-co-3-P[HVIM][Br]和PEG-co-3-P[BVIM][Br]的半数溶血值(HC50)分别在1μg/mL、5μg/mL和100μg/mL左右;抗菌能力随咪唑盐上取代烷基长度的增加而增加。最后通过比较共聚物的HC50值和MIC值,我们发现PEG-co-3-P[BVIM][Br]的HC50(100μg/mL)>MIC(90μg/mL),符合临床医学抗菌药物的要求。
本文最后针对市场上聚乙烯(PE)管和聚丙烯(PP-R)管由于使用银系抗菌剂存在银离子污染的问题,与杭州市联通管业有限公司联合开发了无银抗菌PE管和PP-R供水管(使用高分子抗菌剂)。产品的力学性能和卫生性能达到PE和PP-R的行业标准,另外其抗菌率达100%。实现年产能达1200万元。
Antimicrobial polymers have been widely concerned for their effective and long-term antimicrobial ability. Most of the antimicrobial polymers studied were based on ammonium, phosphonium, pyridinium, organotin, or guanidine, whose applications are limited by their poor thermal stability. Meanwhile, the imidazolium may provide good stability due to its unique five-membered ring structure.
Herein a seris of new imidazolium based antimicrobial polymers were synthesized, and the relationship between the thermal and antimicrobial properties and their structures was investigated. It was found that polymers based on imidazolium, especially those with BF4 and PF6 anion showed good thermal stability with the intial decomposition tempreature upto 350 o C, which was high enough for various applications. The study of the relationship between their structures and antimicrobial activities against E. coli and Staphylococcus aureus indicated that the polymer [poly(3 - dodecyl -1- vinylimidazolium bromide)] with the hydrophobic alkyl chain of 12 CH2 had the best antimicrobial properties, having the MIC values of 33μg/ml against E. coli and 47μg/ml against Staphylococcus aureus. In addition, the types of anions had great effect on the antibacterial with antimicrobial capability order of Br> BF4> PF6.
The imidazolium based antimicrobial polymers were also modified to make antimicrobial drugs. To mimic the structure of antimicrobial peptides, amphiphilic cationic copolymers were designed and synthesized by copolymerization of antimicrobial monomers with hydrophilic PEG including PEG-co-poly(3-butyl-1-vinylimidazolium bromide) (PEG- co-3-P[BVIM][Br]), PEG-co–poly(3-hexyl-1-vinylimidazolium bromide) (PEG-co-3-P[HVIM][Br]), and PEG-co–poly(3-dodecyl-1-vinylimidazolium bromide) (PEG-co-3-P[DDVIM][Br]). The amphiphilic imidazolium cationic polymer self-assembled into nanoparticles in water, and the size of the nanoparticles decrease with the reductionof the hydrophobic alkyl chain length. The volume average hydrodynamic diameter of the nanoparticles made of PEG-co-3-P [BVIM] [Br], PEG-co-3-P[HVIM][Br], and PEG-co-3-P[DDVIM][Br] were 88 nm, 72nm and 19.3nm, respectively. Their blood compatibility, antimicrobial properties were investigagted, indicating that the hemolysis ability of antimicrobial copolymers decreased with the reduction in the alkyl length. with the HC50 for PEG-co-3-P[DDVIM][Br] , PEG-co-3-P[HVIM][Br], PEG-co-3-P [BVIM][Br] of 1μg/mL、5μg/mL and 100μg/mL. Antibacterial ability increased with the increase of the alkyl length. By comparing the HC50 values and MIC values, we find that PEG-co-3-P[BVIM][Br] are promising as antimicrobial drug wih the HC50 (100μg/ml)> MIC (90μg/ml),.
Finially, since most of antimicrobial polyethylene (PE) and polypropylene (PP-R) pipes were made of silver antimicrobial agents with a risk of siliver pollution in water for life, the author in cooperation with Hangzhou Unicom Pipe Co., Ltd, developed antibacterial PE and PP-R pipes by adding antimicrobial polymers instead of silver antimicrobial agents and The health performance and mechanical properties of the antimicrobial PE and PP-R pipes reached industry standard, and their antibacterial rate reached 100%. The productions were successively industrialized with an annual production capacity of 12 million yuan.
本论文首先通过研究抗菌剂的结构与其热稳定性间的关系,发现咪唑盐类高分子抗菌剂尤其是经BF4和PF6离子取代后的抗菌剂具有很好的热稳定性,初始热分解温度高达350 oC,能够满足大部分加工、应用的要求。其次考察了咪唑盐类高分子抗菌剂的结构与其抗菌性能的关系,结果表明:咪唑盐上取代的疏水碳链长度以及不同阴离子种类对抗菌效果有较大的影响。当咪唑盐上取代的疏水碳链长度为12时,抗菌效果最好,过长或过短都会减弱其抗菌能力(其中3-十二烷基-1-乙烯基咪唑溴盐聚合物对大肠杆菌的最小抑菌浓度(MIC)仅为33μg/mL,对金黄色葡萄球菌的MIC值为47μg/mL);不同阴离子种类抗菌剂的抗菌活性顺序为Br>BF4>PF6。
本文还将咪唑盐类高分子抗菌剂应用到高分子抗菌药物这一前沿领域。模仿抗菌多肽的结构,将抗菌剂与亲水的聚乙二醇大分子单体共聚合成了三种阳离子型双亲性共聚合物:PEG-co -3-丁基-1-乙烯基咪唑溴盐聚合物(PEG-co-3- P[BVIM][Br])、PEG-co -3-己基-1-乙烯基咪唑溴盐聚合物(PEG-co-3-P[HVIM][Br]),和PEG-co-3-十二烷基-1-乙烯基咪唑溴盐聚合物(PEG-co-3-P[DDVIM][Br])。并研究了共聚物结构,及其与血液相容性和抗菌性能的关系。结果发现咪唑盐两亲性阳离子聚合物在水中自装成纳米颗粒,纳米颗粒的粒径随疏水烷基链长的变短而变小, PEG-co-3-P[BVIM][Br]、PEG-co-3-P[HVIM][Br]和PEG-co-3-P[DDVIM][Br]形成的纳米颗粒的体积平均粒径分别为88 nm、72 nm和19 nm;抗菌共聚物的溶血性随咪唑盐上取代烷基长度的缩短而减弱。PEG-co-3-P[DDVIM][Br]、PEG-co-3-P[HVIM][Br]和PEG-co-3-P[BVIM][Br]的半数溶血值(HC50)分别在1μg/mL、5μg/mL和100μg/mL左右;抗菌能力随咪唑盐上取代烷基长度的增加而增加。最后通过比较共聚物的HC50值和MIC值,我们发现PEG-co-3-P[BVIM][Br]的HC50(100μg/mL)>MIC(90μg/mL),符合临床医学抗菌药物的要求。
本文最后针对市场上聚乙烯(PE)管和聚丙烯(PP-R)管由于使用银系抗菌剂存在银离子污染的问题,与杭州市联通管业有限公司联合开发了无银抗菌PE管和PP-R供水管(使用高分子抗菌剂)。产品的力学性能和卫生性能达到PE和PP-R的行业标准,另外其抗菌率达100%。实现年产能达1200万元。
Antimicrobial polymers have been widely concerned for their effective and long-term antimicrobial ability. Most of the antimicrobial polymers studied were based on ammonium, phosphonium, pyridinium, organotin, or guanidine, whose applications are limited by their poor thermal stability. Meanwhile, the imidazolium may provide good stability due to its unique five-membered ring structure.
Herein a seris of new imidazolium based antimicrobial polymers were synthesized, and the relationship between the thermal and antimicrobial properties and their structures was investigated. It was found that polymers based on imidazolium, especially those with BF4 and PF6 anion showed good thermal stability with the intial decomposition tempreature upto 350 o C, which was high enough for various applications. The study of the relationship between their structures and antimicrobial activities against E. coli and Staphylococcus aureus indicated that the polymer [poly(3 - dodecyl -1- vinylimidazolium bromide)] with the hydrophobic alkyl chain of 12 CH2 had the best antimicrobial properties, having the MIC values of 33μg/ml against E. coli and 47μg/ml against Staphylococcus aureus. In addition, the types of anions had great effect on the antibacterial with antimicrobial capability order of Br> BF4> PF6.
The imidazolium based antimicrobial polymers were also modified to make antimicrobial drugs. To mimic the structure of antimicrobial peptides, amphiphilic cationic copolymers were designed and synthesized by copolymerization of antimicrobial monomers with hydrophilic PEG including PEG-co-poly(3-butyl-1-vinylimidazolium bromide) (PEG- co-3-P[BVIM][Br]), PEG-co–poly(3-hexyl-1-vinylimidazolium bromide) (PEG-co-3-P[HVIM][Br]), and PEG-co–poly(3-dodecyl-1-vinylimidazolium bromide) (PEG-co-3-P[DDVIM][Br]). The amphiphilic imidazolium cationic polymer self-assembled into nanoparticles in water, and the size of the nanoparticles decrease with the reductionof the hydrophobic alkyl chain length. The volume average hydrodynamic diameter of the nanoparticles made of PEG-co-3-P [BVIM] [Br], PEG-co-3-P[HVIM][Br], and PEG-co-3-P[DDVIM][Br] were 88 nm, 72nm and 19.3nm, respectively. Their blood compatibility, antimicrobial properties were investigagted, indicating that the hemolysis ability of antimicrobial copolymers decreased with the reduction in the alkyl length. with the HC50 for PEG-co-3-P[DDVIM][Br] , PEG-co-3-P[HVIM][Br], PEG-co-3-P [BVIM][Br] of 1μg/mL、5μg/mL and 100μg/mL. Antibacterial ability increased with the increase of the alkyl length. By comparing the HC50 values and MIC values, we find that PEG-co-3-P[BVIM][Br] are promising as antimicrobial drug wih the HC50 (100μg/ml)> MIC (90μg/ml),.
Finially, since most of antimicrobial polyethylene (PE) and polypropylene (PP-R) pipes were made of silver antimicrobial agents with a risk of siliver pollution in water for life, the author in cooperation with Hangzhou Unicom Pipe Co., Ltd, developed antibacterial PE and PP-R pipes by adding antimicrobial polymers instead of silver antimicrobial agents and The health performance and mechanical properties of the antimicrobial PE and PP-R pipes reached industry standard, and their antibacterial rate reached 100%. The productions were successively industrialized with an annual production capacity of 12 million yuan.
引文
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