含辣素衍生结构单体及其聚合物的合成与海洋防污性能研究
摘要
本论文研究了含辣素衍生结构单体及其聚合物的合成与海洋防污应用性能。通过对辣素等天然防污活性物质进行结构分析,设计出含辣素衍生结构单体,较系统地研究了含辣素衍生结构单体的合成；以含辣素衍生结构单体为功能单体,系统地研究了含辣素衍生结构丙烯酸树脂的合成；并通过红外光谱、核磁共振谱等仪器分析手段对所合成化合物和聚合物进行结构表征和确认。
以含辣素衍生结构单体为防污剂制备海洋防污涂料,并将含辣素衍生结构的丙烯酸树脂进行实海挂板,较系统的研究了新得到化合物和树脂的防污性能。通过抑菌圈和最小抑菌浓度进行抑菌性能的研究。含辣素衍生结构苯甲酰胺单体中以HMBB, HBOMB和BHMBB1的抑菌效果最好,同样在含辣素衍生结构氯乙酰胺单体中CPHBC具有最好的抑菌效果,而含辣素衍生结构丙烯酰胺的两种单体的抑菌效果也是较理想的。海上挂板实验结果表明,新合成19个含辣素功能结构单体作为防污剂添加到防污涂料中,经过5个月的实海挂板均表现出较好的防污效果,其中试片435、436、437、438和439(分别含有功能单体HMBB、HBOMB、BHMBB1、BHMBB和AHMBA)均表现出较好的防污效果,所得结果与抑菌实验所得结果基本一致。同时将含辣素衍生结构丙烯酸树脂在大型污损生物藤壶生长的旺季进行长达2个月的实海挂板,可以看出含BHMBA的树脂对海洋污损生物均表现出一定的抑制作用,以BHMBA-SA树脂和BHMBA-BA-MMA树脂效果较好,并对大型污损生物藤壶具有较好的抑制作用。
As concerning the high toxicity of organotin paints, the need to develop new environment-friendly antifouling paints has been highlighted. The tin-free acrylic polymers used play a very significant role in the processing and end-used behaviour of the antifouling paints.
Capsaicin, Ceratinamine, Pseudoceratidine, tribromogramine(TBG) natural products are a structurally diverse class of metabolites embodying a broad spectrum of interesting biological activities. Many analogs of Capsaicin, Ceratinamine, Pseudoceratidine and tribromogramine have been found to be cytotoxic, as well as antibacterial, anti-HIV and antifouling.
In this paper, the uniquely functionalized antifoulant monomers derived from natural products above mentioned were designed and synthesized. And also their copolymers were synthesized. Furthermore, all the monomers and their polymers were characterized by FTIR and 1HNMR. After that, two types of marine antifouling paints are prepared with newly synthesized monomers as antifoulant and their polymers as binder resins, respectively.
Antibacterial properties were carried out by the experiments of inhibition zone and minimal inhibitory concentration. HMBB, HBOMB and BHMBB1 have the best antibacterial activities among benzamide monomers containing capsaicin derivatives, and so is CPHBC among chloroacetamide monomers containing capsaicin derivatives, and two acrylamide monomers containing capsaicin derivatives also have desirable bacteriostasic activity. And also the paint used newly prepared nineteen monomers as antifoulant were examined in the sea for five months. The results suggested that the paints with HMBB、HBOMB、BHMBB1、BHMBB and AHMBA all had desirable antifouling properties, and the results was the same with bacteriostasic experiment. And also the polymers containing capsaicin derivative were examined in the sea for one month especially in the period of a good stanf of barnacle, in the study, we could see resin with BHMBA have good inhibition activities among others, and BHMBA-SA resin and BHMBA-BA-MMA had better effect especially to macroantifouling organism barnacle.
以含辣素衍生结构单体为防污剂制备海洋防污涂料,并将含辣素衍生结构的丙烯酸树脂进行实海挂板,较系统的研究了新得到化合物和树脂的防污性能。通过抑菌圈和最小抑菌浓度进行抑菌性能的研究。含辣素衍生结构苯甲酰胺单体中以HMBB, HBOMB和BHMBB1的抑菌效果最好,同样在含辣素衍生结构氯乙酰胺单体中CPHBC具有最好的抑菌效果,而含辣素衍生结构丙烯酰胺的两种单体的抑菌效果也是较理想的。海上挂板实验结果表明,新合成19个含辣素功能结构单体作为防污剂添加到防污涂料中,经过5个月的实海挂板均表现出较好的防污效果,其中试片435、436、437、438和439(分别含有功能单体HMBB、HBOMB、BHMBB1、BHMBB和AHMBA)均表现出较好的防污效果,所得结果与抑菌实验所得结果基本一致。同时将含辣素衍生结构丙烯酸树脂在大型污损生物藤壶生长的旺季进行长达2个月的实海挂板,可以看出含BHMBA的树脂对海洋污损生物均表现出一定的抑制作用,以BHMBA-SA树脂和BHMBA-BA-MMA树脂效果较好,并对大型污损生物藤壶具有较好的抑制作用。
As concerning the high toxicity of organotin paints, the need to develop new environment-friendly antifouling paints has been highlighted. The tin-free acrylic polymers used play a very significant role in the processing and end-used behaviour of the antifouling paints.
Capsaicin, Ceratinamine, Pseudoceratidine, tribromogramine(TBG) natural products are a structurally diverse class of metabolites embodying a broad spectrum of interesting biological activities. Many analogs of Capsaicin, Ceratinamine, Pseudoceratidine and tribromogramine have been found to be cytotoxic, as well as antibacterial, anti-HIV and antifouling.
In this paper, the uniquely functionalized antifoulant monomers derived from natural products above mentioned were designed and synthesized. And also their copolymers were synthesized. Furthermore, all the monomers and their polymers were characterized by FTIR and 1HNMR. After that, two types of marine antifouling paints are prepared with newly synthesized monomers as antifoulant and their polymers as binder resins, respectively.
Antibacterial properties were carried out by the experiments of inhibition zone and minimal inhibitory concentration. HMBB, HBOMB and BHMBB1 have the best antibacterial activities among benzamide monomers containing capsaicin derivatives, and so is CPHBC among chloroacetamide monomers containing capsaicin derivatives, and two acrylamide monomers containing capsaicin derivatives also have desirable bacteriostasic activity. And also the paint used newly prepared nineteen monomers as antifoulant were examined in the sea for five months. The results suggested that the paints with HMBB、HBOMB、BHMBB1、BHMBB and AHMBA all had desirable antifouling properties, and the results was the same with bacteriostasic experiment. And also the polymers containing capsaicin derivative were examined in the sea for one month especially in the period of a good stanf of barnacle, in the study, we could see resin with BHMBA have good inhibition activities among others, and BHMBA-SA resin and BHMBA-BA-MMA had better effect especially to macroantifouling organism barnacle.
引文
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