含辣素衍生结构的丙烯酰胺单体与聚合物的合成及其海洋防污应用性能研究
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摘要
本论文研究了含辣素衍生结构的丙烯酰胺单体与聚合物的合成及其海洋防污应用性能。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的丙烯酰胺单体,较系统地研究了含辣素衍生结构的丙烯酰胺单体的合成;以含辣素衍生结构的丙烯酰胺单体为功能单体,较系统地研究了含辣素衍生结构的丙烯酸树脂的合成;并通过红外光谱、核磁共振谱等仪器分析手段对合成化合物或材料进行了表征和确认;分别以含辣素衍生结构的丙烯酰胺为防污剂、以含辣素衍生结构的丙烯酸树脂为成膜物质制备两类防污涂料。
较系统地对新合成的化合物或材料进行了防污性能研究。在室内紫贻贝附着抑制性实验中发现,含辣素衍生结构的丙烯酰胺单体抑制活性相对大小排序为:HMMBA>HMTBA>CHBA≈HMBA>BHBA>HDMBA>TMBA>DMBA≈AMBMA。在室内新月菱形藻抑制性实验中发现,含辣素衍生结构的丙烯酰胺单体抑制活性相对大小排序为: HDMBA>DMBA≈BMA>TMBA≈HMTBA>CHBA>HMMBA>BHBA>HMBA;含辣素衍生结构的丙烯酸树脂对新月菱形藻附着均表现出明显的抑制性,其附着抑制率均大于22%,最高可达53%。海上挂板实验表明,在考察时期内,当功能单体含量为30%时,含辣素衍生结构的丙烯酸树脂对藻类附着抑制性的大小顺序为:HMBA丙烯酸树脂> TMBA丙烯酸树脂> HMMBA丙烯酸树脂>普通丙烯酸树脂;以含辣素衍生结构的丙烯酰胺单体为防污剂的海洋防污涂料和以对含辣素衍生结构的丙烯酸树脂为成膜物的海洋防污涂料均表现出一定的防污性。以含辣素衍生结构的丙烯酰胺为防污剂的防污涂料,在考察时间内各防污剂对藻类附着的抑制性大小顺序为:TMBA>HDMBA>CHBA>HMBA>HMMBA。在短期内各防污剂对生物粘膜形成抑制性大小顺序为:HDMBA> TMBA> CHBA >HMBA >HMBA,而长期则为TMBA>HDMBA>CHBA > HMBA>HMBA。
另外,还系统地研究了HMBA凝胶和AMBMA凝胶的合成和性能。
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 acrylamide monomers derived from natural products above mentioned are designed and synthesized. And also their copolymers with acrylates are synthesized. Furthermore, all of the monomers and their copolymers are characterized by FTIR and NMR. After that, two types of marine antifouling paints are prepared with newly synthesized monomers as antifoulant and their copolymers as binder resins, respectively.
For those newly synthesized monomers, the attachment inhibition assay against the blue Mussel (Mytilus edulis) in the laboratory appears to be in the order HMMBA>HMTBA>CHBA≈HMBA>BHBA>HDMBA>TMBA>DMBA≈AMBMA. And in the laboratory growth inhibition assay against the Nitzschia closterium shows in the order HDMBA>DMBA≈BMA>TMBA≈HMTBA>CHBA>HMMBA>BHBA>HMBA. As for those copolymers, the percentage inhibition of the Nitzschia closterium settlement in the laboratory was from 22% to 53%. And also the newly prepared copolymers and paints are examined in the sea. The results suggest that both the copolymers and paints have an antifouling effect on fouling organisms. The copolymers with 30% functional monomer units exhibit in the order HMBA acrylate resin > TMBA acrylate resin> HMMBA acrylate resin > common acrylate in the settlement inhibition against algae in the sea. And the paints with functional acrylamide monomers as antifoulant show in the order TMBA>HDMBA>CHBA>HMBA>
较系统地对新合成的化合物或材料进行了防污性能研究。在室内紫贻贝附着抑制性实验中发现,含辣素衍生结构的丙烯酰胺单体抑制活性相对大小排序为:HMMBA>HMTBA>CHBA≈HMBA>BHBA>HDMBA>TMBA>DMBA≈AMBMA。在室内新月菱形藻抑制性实验中发现,含辣素衍生结构的丙烯酰胺单体抑制活性相对大小排序为: HDMBA>DMBA≈BMA>TMBA≈HMTBA>CHBA>HMMBA>BHBA>HMBA;含辣素衍生结构的丙烯酸树脂对新月菱形藻附着均表现出明显的抑制性,其附着抑制率均大于22%,最高可达53%。海上挂板实验表明,在考察时期内,当功能单体含量为30%时,含辣素衍生结构的丙烯酸树脂对藻类附着抑制性的大小顺序为:HMBA丙烯酸树脂> TMBA丙烯酸树脂> HMMBA丙烯酸树脂>普通丙烯酸树脂;以含辣素衍生结构的丙烯酰胺单体为防污剂的海洋防污涂料和以对含辣素衍生结构的丙烯酸树脂为成膜物的海洋防污涂料均表现出一定的防污性。以含辣素衍生结构的丙烯酰胺为防污剂的防污涂料,在考察时间内各防污剂对藻类附着的抑制性大小顺序为:TMBA>HDMBA>CHBA>HMBA>HMMBA。在短期内各防污剂对生物粘膜形成抑制性大小顺序为:HDMBA> TMBA> CHBA >HMBA >HMBA,而长期则为TMBA>HDMBA>CHBA > HMBA>HMBA。
另外,还系统地研究了HMBA凝胶和AMBMA凝胶的合成和性能。
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 acrylamide monomers derived from natural products above mentioned are designed and synthesized. And also their copolymers with acrylates are synthesized. Furthermore, all of the monomers and their copolymers are characterized by FTIR and NMR. After that, two types of marine antifouling paints are prepared with newly synthesized monomers as antifoulant and their copolymers as binder resins, respectively.
For those newly synthesized monomers, the attachment inhibition assay against the blue Mussel (Mytilus edulis) in the laboratory appears to be in the order HMMBA>HMTBA>CHBA≈HMBA>BHBA>HDMBA>TMBA>DMBA≈AMBMA. And in the laboratory growth inhibition assay against the Nitzschia closterium shows in the order HDMBA>DMBA≈BMA>TMBA≈HMTBA>CHBA>HMMBA>BHBA>HMBA. As for those copolymers, the percentage inhibition of the Nitzschia closterium settlement in the laboratory was from 22% to 53%. And also the newly prepared copolymers and paints are examined in the sea. The results suggest that both the copolymers and paints have an antifouling effect on fouling organisms. The copolymers with 30% functional monomer units exhibit in the order HMBA acrylate resin > TMBA acrylate resin> HMMBA acrylate resin > common acrylate in the settlement inhibition against algae in the sea. And the paints with functional acrylamide monomers as antifoulant show in the order TMBA>HDMBA>CHBA>HMBA>
引文
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