受阻胺类光稳定剂的设计、合成及表征
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摘要
受阻胺类光稳定剂由于其优异的光稳定性能,一直是国内外光稳定剂研究开发的热点之一。本文研究建立了三个受阻胺类光稳定剂的合成工艺,探索了聚合型受阻胺类光稳定剂生产过程中不溶性副产物产生的原因,并设计、合成了一系列具有抑菌活性的新型受阻胺类光稳定剂。
1、在研究癸二酸二甲酯与1,2,2,6,6-五甲基哌啶醇的酯交换反应的基础上,建立了受阻胺类光稳定剂Tinuvin292、Tinuvin765的合成工艺,分别以93.3%和92.4%的收率得到了光稳定剂Tinuvin292、Tinuvin765,所得产品质量达到了国外同类产品的水平。
2、研究建立了受阻胺类光稳定剂Tinuvin123的合成工艺。以2,2,6,6-四甲基哌啶醇为原料,经氧化、自由基和酯交换三步反应以57.6%的总收率得到了产品。利用1H NMR对其结构进行的分析和表征,本工艺所得产品的组成与国外同类产品组成一致。
3、根据对聚合型受阻胺类光稳定剂Cyasorb3346和Chimassorb944合成工艺的研究,提出了其生产过程中不溶性副产物可能的结构。在此推断的基础上,合成了5个化合物,并利用1H NMR、13 C NMR、ESI-MS对其结构进行了表征。与分离出的不溶性副产物主要成分的结构表征对比表明,化合物5a-b分别是Cyasorb3346和Chimassorb944生产过程中的不溶性副产物。
4、本文将N-卤结构引入反应型HALS的分子结构中,合成了具有杀菌活性的一类新型受阻胺类光稳定剂。利用1 H NMR、IR、ESI-MS对其结构进行了表征。对其进行的抑菌活性实验表明:在0.05%的浓度下,所有目标化合物对白色念珠菌Candida albicans,金黄色葡萄球菌Staphylococcus aureus和大肠杆菌Escherichia coli都有较好的抑菌活性。
Hindered amine light stabilizers are always one of the most attractive fields of stabilizers due to their excellent photo-stabilization efficiency. The synthetic technologies of three hindered amine light stabilizers were established, the reason for the insoluble side products formed in the production of polymerized hindered amine light stabilizers were studied, and a series of novel hindered amine light stabilizers with antibacterial properties were designed and synthesized in this present paper.
1. Based on the investigation of the transesterification between dimethyl sebacate and 1,2,2,6,6-pentamethyl-4-piperinol, the synthetic technologies of Tinuvin292 and Tinuvin 765 were established. The two kinds of hindered amine light stabilizers were obtained in the yield of 93.3% and 92.4% respectively and qualified as the advanced level of the kindred overseas products.
2. The synthetic technology of Tinuvin123 was studied and established. Using 2,2,6,6-tetramethyl-4-piperinol as the starting material, the product was synthesized successfully through oxidation, free-radical reaction and transesterification in overall yield of 57.6%. According to the characterization of the obtained Tinuvin123 by 1H NMR, its composition was identical to those of the kindred overseas products.
3. This dissertation theorized the structures of the insoluble side products formed in the production of Cyasorb3346 and Chimassorb944 according to the investigation of their synthetic technologies. Based on this hypothesis, five compounds were synthesized and their structures were confirmed by 1H NMR, 13C NMR and ESI-MS. The by-products obtained during the production of Cyasorb3346 and Chimassorb944 were separated and purified, their spectra were recorded, indicating that 5a-b were the main insoluble by-products during the production of Cyasorb3346 and Chimassorb944.
4. This dissertation introduced an N-halamine structure to a reactive-HALS molecule resulting in a new type of hindered amine light stabilizers capable of providing both photo-stabilization and antimicrobial activity. Their structures were characterized by FT-IR, 1H NMR, and ESI-MS. The compounds were tested for antibacterial activity against Candida albicans, Staphylococcus aureus, and Escherichia coli. At a concentration of 0.05%, these compounds all exhibited satisfactory antibacterial activity against all the three types of bacteria.
1、在研究癸二酸二甲酯与1,2,2,6,6-五甲基哌啶醇的酯交换反应的基础上,建立了受阻胺类光稳定剂Tinuvin292、Tinuvin765的合成工艺,分别以93.3%和92.4%的收率得到了光稳定剂Tinuvin292、Tinuvin765,所得产品质量达到了国外同类产品的水平。
2、研究建立了受阻胺类光稳定剂Tinuvin123的合成工艺。以2,2,6,6-四甲基哌啶醇为原料,经氧化、自由基和酯交换三步反应以57.6%的总收率得到了产品。利用1H NMR对其结构进行的分析和表征,本工艺所得产品的组成与国外同类产品组成一致。
3、根据对聚合型受阻胺类光稳定剂Cyasorb3346和Chimassorb944合成工艺的研究,提出了其生产过程中不溶性副产物可能的结构。在此推断的基础上,合成了5个化合物,并利用1H NMR、13 C NMR、ESI-MS对其结构进行了表征。与分离出的不溶性副产物主要成分的结构表征对比表明,化合物5a-b分别是Cyasorb3346和Chimassorb944生产过程中的不溶性副产物。
4、本文将N-卤结构引入反应型HALS的分子结构中,合成了具有杀菌活性的一类新型受阻胺类光稳定剂。利用1 H NMR、IR、ESI-MS对其结构进行了表征。对其进行的抑菌活性实验表明:在0.05%的浓度下,所有目标化合物对白色念珠菌Candida albicans,金黄色葡萄球菌Staphylococcus aureus和大肠杆菌Escherichia coli都有较好的抑菌活性。
Hindered amine light stabilizers are always one of the most attractive fields of stabilizers due to their excellent photo-stabilization efficiency. The synthetic technologies of three hindered amine light stabilizers were established, the reason for the insoluble side products formed in the production of polymerized hindered amine light stabilizers were studied, and a series of novel hindered amine light stabilizers with antibacterial properties were designed and synthesized in this present paper.
1. Based on the investigation of the transesterification between dimethyl sebacate and 1,2,2,6,6-pentamethyl-4-piperinol, the synthetic technologies of Tinuvin292 and Tinuvin 765 were established. The two kinds of hindered amine light stabilizers were obtained in the yield of 93.3% and 92.4% respectively and qualified as the advanced level of the kindred overseas products.
2. The synthetic technology of Tinuvin123 was studied and established. Using 2,2,6,6-tetramethyl-4-piperinol as the starting material, the product was synthesized successfully through oxidation, free-radical reaction and transesterification in overall yield of 57.6%. According to the characterization of the obtained Tinuvin123 by 1H NMR, its composition was identical to those of the kindred overseas products.
3. This dissertation theorized the structures of the insoluble side products formed in the production of Cyasorb3346 and Chimassorb944 according to the investigation of their synthetic technologies. Based on this hypothesis, five compounds were synthesized and their structures were confirmed by 1H NMR, 13C NMR and ESI-MS. The by-products obtained during the production of Cyasorb3346 and Chimassorb944 were separated and purified, their spectra were recorded, indicating that 5a-b were the main insoluble by-products during the production of Cyasorb3346 and Chimassorb944.
4. This dissertation introduced an N-halamine structure to a reactive-HALS molecule resulting in a new type of hindered amine light stabilizers capable of providing both photo-stabilization and antimicrobial activity. Their structures were characterized by FT-IR, 1H NMR, and ESI-MS. The compounds were tested for antibacterial activity against Candida albicans, Staphylococcus aureus, and Escherichia coli. At a concentration of 0.05%, these compounds all exhibited satisfactory antibacterial activity against all the three types of bacteria.
引文
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