通过Friedel-Crafts烷基化反应制备POSS基杂化材料及性能研究
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摘要
笼型聚硅氧烷(POSS)具有优异的热稳定性、化学稳定性,低介电性能,较好的生物相容性等特点,被广泛地应用于制备各种有机-无机杂化材料,是材料科学不可或缺的重要组成部分。拓宽功能化的POSS单体的制备方法,开发新型的POSS杂化材料具有重要的理论意义及应用价值。本文围绕两个方面进行研究：一、首先利用Friedel-Crafts烷基化反应制备八苯乙基POSS,然后通过物理共混的方法,制备新型的聚合物/POSS杂化材料；二、利用八乙烯基POSS和具有不同空间构型的芳香族单体为构筑单元,通过Friedel-Crafts烷基化反应制备出一系列的POSS基多孔聚合物。具体内容如下。
1.利用八乙烯基POSS和苯为原料,通过Friedel-Crafts烷基反应,得到了八苯乙基POSS。通过物理共混得到了基于酚醛树脂和八苯乙基POSS的杂化材料。用FT-IR、POM、XRD以及DSC等手段对固化前的酚醛树脂/POSS杂化材料的氢键作用、形貌、物相形态和相容性进行研究。结果表明：POSS与酚醛树脂之间存在着氢键作用,在POSS含量低于20wt%时,POSS能够与酚醛树脂形成均一的相；随着POSS含量的持续增加,POSS开始团聚,体系出现了相分离。利用六次甲基四胺固化了酚醛树脂/POSS杂化材料,用FT-IR和SEM研究了固化后POSS与酚醛树脂之间的相容性。结果表明：固化促使POSS与酚醛树脂的相分离。用DMA和TGA考察了POSS对固化后酚醛树脂/POSS杂化材料的机械性能和热性能的影响。
2.利用八乙烯基POSS和苯为原料,通过Friedel-Crafts烷基反应,成功地制备出新型POSS基多孔聚合物。用元素分析、FT-IR、13C CP/MAS NMR和29Si CP/MAS NMR等测试手段对多孔聚合物的组成和结构进行了确认。用N2吸附-脱附实验对其孔结构参数进行表征。结果表明：HPP-1至HPP-4的比表面积在400～900m2g-1之间,孔体积在0.24～0.99cm3g-1之间。通过调节链接单元苯的用量,成功地实现了对多孔聚合物的孔结构参数的调控；给出了多孔聚合物孔结构参数的调控机理。另外采用XRD、FE-SEM、HRTEM以及TGA等测试手段,对多孔聚合物的物相形态、形貌和热性能进行了表征。结果表明：得到的多孔聚合物是一种无定形的、介孔和微孔共存的多孔聚合物,且具有较高的热稳定性能。采用H2和CO2的等温吸附实验对多孔聚合物的气体吸附性能进行了研究。结果表明：多孔聚合物具有较好的H2和C02的吸附性能。最后通过Thiol-ene Click Reaction反应对得到的多孔聚合物进行了后功能化,并对功能化后的多孔聚合物的结构和性能进行了表征。
3.利用八乙烯基POSS分别和非平面型小分子联苯、1,3,5-三苯基苯为原料,通过Friedel-Crafts烷基反应,成功合成出新型POSS基多孔聚合物。用元素分析、FT-IR、13C CP/MAS NMR和29Si CP/MAS NMR等测试手段对多孔聚合物的组成和结构进行了确认。用N2吸附-脱附实验对其孔结构参数进行表征。结果表明：HPP-2、HPP-3、HPP-4、HPP-6、HPP-7、HPP-8的比表面积在600-900m2g-1之间,孔体积分别在0.51～0.55cm3g-1之间和0.55～0.76cm3g-1之间。通过控制非平面型分子的用量虽然可以调节多孔聚合物的比表面积,但是对其孔体积的影响很小。采用TGA、XRD、FE-SEM和HRTEM等测试手段,对多孔聚合物的热稳定性、物相形态、形貌进行了表征。结果表明：多孔聚合物是一种无定形的,介孔与微孔共存的多孔材料。采用H2和CO2的吸等温吸附实验对多孔聚合物的气体吸附性能进行了研究。结果表明：与其他比表面积相似的其他的POSS基多孔聚合物相比,实验中所制备的多孔聚合物表现出较高的CO2吸附性能。
4.利用八乙烯基POSS与聚苯乙烯作为构筑单元,通过Friedel-Crafts烷基化反应,成功地制备出具有网络结构的POSS基多孔聚合物。用FT-IR、13C CP/MAS NMR和29Si CP/MAS NMR等测试手段对多孔聚合物的组成和结构进行了确认。用N2吸附-脱附实验对其孔结构参数进行表征。结果表明：HPP-1至HPP-7的比表面积在12～770m2g-1之间,孔体积分别在0.36～0.90cm3g-1之间。探讨了多孔聚合物的孔结构参数的变化规律及其形成机理。采用TGA,FE-SEM和HRTEM等测试手段,对多孔聚合物的热性能和形貌进行了分析。结果表明,多孔聚合物是无定形的,介孔与微孔共存的多孔聚合物。采用H2和C02的等温吸附实验对多孔聚合物的气体吸附性能研究了研究。结果表明：多孔聚合物具有较好的H2和CO2的吸附性能。
Polyhedral oligomeric silsesquioxanes (POSS) are novel kind of nano-scale inorganic-organic hybrids and they have been widely used to prepare varieties of POSS-based polymers and POSS-containing functional materials due to their unique characteristics of thermal stability, chemical stability, low dielectric properties and excellent biocompatibility. The study of POSS is an important integral part of nanocomposites. It has great significance in theory and application to select the new method for preparing the novel POSS monomers, developing the high performance POSS-based polymers and especially developing the POSS-containing polymers with special functionalities. In the present dissertation, two aspects had been focused. One was to prepare octaphenethyl POSS via the Friedel-Crafts alkylation reaction and use it to develop the novel POSS-based polymers. The other was to synthsize a series of POSS-based functional materials and particularly preparing the porous POSS-containing polymers through the Friedel-Crafts alkylation reaction.
1. The octaphenethyl POSS was prepared via Friedel-Crafts reaction by using octavinyl POSS and benzene as the starting materials. The POSS-based nanocomposites were prepared by solution blending of novolac resin and octaphenethyl POSS. FT-IR, POM, XRD and DSC were used to characterize the specific hydrogen bonding interaction, morphology and miscibility of phenolicresin/POSS nanocomposites before curing. The results indicated that there existed intermolecular hydrogen bonding interactions between the hydroxyl groups of the phenolic resin and Si-O-Si groups of POSS, which could promote POSS to disperse well in the polymer matrix up to20wt%POSS loading. At higher POSS loading, POSS would aggregate and lead to macrophase separation. Finally, the hexamethylene tetramine was used to cure the phenolic resin/POSS nanocomposites to form the network structure. The miscibility was also characterized by FT-IR and SEM. The results showed that the curing process prompted phase separation between the phenolic resin and POSS particles. DMA and TGA were also used to perform the thermal stability and mechanical properties of the cured phenolic resin/POSS nanocomposites.
2. A series of hybrid porous polymers (HPPs) were prepared via Friedel-Crafts reaction by using octavinyl POSS and benzene as the starting materials. The structures of hybrid porous polymers were characterized by FT-IR,13C CP/MAS NMR and29Si CP/MAS NMR. The porosities of hybrid porous polymers were determined by the N2sorption-desorption isotherms. The results showed that hybrid porous polymers featured both micro-and mesopores with apparent Brunauer-Emmett-Teller surface areas in a range of400～904m2g-1, with total pore volumes in the range of0.24cm3g-1to0.99cm3g-1. Their porosities can be fine tuned by adjusting the mole ratios of octavinyl POSS and benzene. The XRD, FE-SEM, HRTEM and TGA were also used to perform the morphologies and thermal stabilities of the hybrid porous polymers. The results showed that these polymers were amorphous porous polymers with high thermal stabilities. H2and CO2gas sorption isotherms were used to perform the sorption properties of the porous hybrid polymers. The results showed that the hybrids had preferable sorption properties and could be potentially applied to H2and CO2gas sorption. Finally, the hybrid porous polymers were postfunctionalized via the Thiol-ene Click reaction. The structures and properties of the postfunctionalised hybrid porous polymers were also characterized.
3. Eight kinds of the hybrid porous polymers were constructed by using octavinyl POSS and the non-planar molecules of biphenyl and1,3,5-triphenylbenzene via Friedel-Crafts alkylation, respectively. The structures of hybrid porous polymers were characterized by FT-IR,13C CP/MAS NMR and29Si CP/MAS NMR. And the porosities of hybrid porous polymers were tested by the N2sorption-desorption isotherms. The results showed that all hybrid porous polymers HPP-2, HPP-3, HPP-4, HPP-6, HPP-7and HPP-8, featured both micro-and mesopores with apparent Brunauer-Emmett-Teller surface areas in a range of600m2g-1to905m2g-1. The total pore volumes were in the range of0.51cm3g-1to0.55cm3g-1and0.55cm3g-1to0.76cm3g-1, respectively. As far as the hybrid porous polymers synthesized with the same building units, the total pore volumes of the hybrid porous polymers were similar, although the SBET of the hybrid porous polymers can be tuned by adjusting mole ratios of octavinyl POSS and non-planar molecules. The XRD, TGA, FE-SEM, HRTEM were also used to perform the thermal stabities and the morphologies of the hybrid porous polymers. The results show that hybrid porous polymers were featured micro-and mesopores, amorphous polmers with high thermal stability. Gas sorption isotherms were also used to characterize the performaces of the H2and CO2sorption properties of the hybrid porous polymers.
4. A variety of hyper-crosslinking polystyrene hybrids were prepared by using octavinyl POSS and polystyrene as building blocks via the Friedel-Crafts alkylation reaction. The structures of polystyrene hybrids porous polymers were characterized by FT-IR,13C CP/MAS NMR and29Si CP/MAS NMR. And the porosities of polystyrene hybrids were investigated by the N2sorption-desorption isotherms. The results show that hybrid porous polymers HPP-1, HPP-2, HPP-6and HPP-7featured both micro-and mesopores with SBET in a range of473m2g-1to767m2g-1, with total pore volumes in the range of0.36cm3g-1to0.90cm3g-1. The TGA, FE-SEM, HRTEM were also used to analyze the thermal stabities and the morphologies of the hybrid porous polymers. The results showed that hybrid porous polymers were amorphous polymers featured micro-and mesopores. Gas sorption isotherms were also used to characterize the performaces of the H2and CO2sorption properties of the hybrid porous polymers.
1.利用八乙烯基POSS和苯为原料,通过Friedel-Crafts烷基反应,得到了八苯乙基POSS。通过物理共混得到了基于酚醛树脂和八苯乙基POSS的杂化材料。用FT-IR、POM、XRD以及DSC等手段对固化前的酚醛树脂/POSS杂化材料的氢键作用、形貌、物相形态和相容性进行研究。结果表明：POSS与酚醛树脂之间存在着氢键作用,在POSS含量低于20wt%时,POSS能够与酚醛树脂形成均一的相；随着POSS含量的持续增加,POSS开始团聚,体系出现了相分离。利用六次甲基四胺固化了酚醛树脂/POSS杂化材料,用FT-IR和SEM研究了固化后POSS与酚醛树脂之间的相容性。结果表明：固化促使POSS与酚醛树脂的相分离。用DMA和TGA考察了POSS对固化后酚醛树脂/POSS杂化材料的机械性能和热性能的影响。
2.利用八乙烯基POSS和苯为原料,通过Friedel-Crafts烷基反应,成功地制备出新型POSS基多孔聚合物。用元素分析、FT-IR、13C CP/MAS NMR和29Si CP/MAS NMR等测试手段对多孔聚合物的组成和结构进行了确认。用N2吸附-脱附实验对其孔结构参数进行表征。结果表明：HPP-1至HPP-4的比表面积在400～900m2g-1之间,孔体积在0.24～0.99cm3g-1之间。通过调节链接单元苯的用量,成功地实现了对多孔聚合物的孔结构参数的调控；给出了多孔聚合物孔结构参数的调控机理。另外采用XRD、FE-SEM、HRTEM以及TGA等测试手段,对多孔聚合物的物相形态、形貌和热性能进行了表征。结果表明：得到的多孔聚合物是一种无定形的、介孔和微孔共存的多孔聚合物,且具有较高的热稳定性能。采用H2和CO2的等温吸附实验对多孔聚合物的气体吸附性能进行了研究。结果表明：多孔聚合物具有较好的H2和C02的吸附性能。最后通过Thiol-ene Click Reaction反应对得到的多孔聚合物进行了后功能化,并对功能化后的多孔聚合物的结构和性能进行了表征。
3.利用八乙烯基POSS分别和非平面型小分子联苯、1,3,5-三苯基苯为原料,通过Friedel-Crafts烷基反应,成功合成出新型POSS基多孔聚合物。用元素分析、FT-IR、13C CP/MAS NMR和29Si CP/MAS NMR等测试手段对多孔聚合物的组成和结构进行了确认。用N2吸附-脱附实验对其孔结构参数进行表征。结果表明：HPP-2、HPP-3、HPP-4、HPP-6、HPP-7、HPP-8的比表面积在600-900m2g-1之间,孔体积分别在0.51～0.55cm3g-1之间和0.55～0.76cm3g-1之间。通过控制非平面型分子的用量虽然可以调节多孔聚合物的比表面积,但是对其孔体积的影响很小。采用TGA、XRD、FE-SEM和HRTEM等测试手段,对多孔聚合物的热稳定性、物相形态、形貌进行了表征。结果表明：多孔聚合物是一种无定形的,介孔与微孔共存的多孔材料。采用H2和CO2的吸等温吸附实验对多孔聚合物的气体吸附性能进行了研究。结果表明：与其他比表面积相似的其他的POSS基多孔聚合物相比,实验中所制备的多孔聚合物表现出较高的CO2吸附性能。
4.利用八乙烯基POSS与聚苯乙烯作为构筑单元,通过Friedel-Crafts烷基化反应,成功地制备出具有网络结构的POSS基多孔聚合物。用FT-IR、13C CP/MAS NMR和29Si CP/MAS NMR等测试手段对多孔聚合物的组成和结构进行了确认。用N2吸附-脱附实验对其孔结构参数进行表征。结果表明：HPP-1至HPP-7的比表面积在12～770m2g-1之间,孔体积分别在0.36～0.90cm3g-1之间。探讨了多孔聚合物的孔结构参数的变化规律及其形成机理。采用TGA,FE-SEM和HRTEM等测试手段,对多孔聚合物的热性能和形貌进行了分析。结果表明,多孔聚合物是无定形的,介孔与微孔共存的多孔聚合物。采用H2和C02的等温吸附实验对多孔聚合物的气体吸附性能研究了研究。结果表明：多孔聚合物具有较好的H2和CO2的吸附性能。
Polyhedral oligomeric silsesquioxanes (POSS) are novel kind of nano-scale inorganic-organic hybrids and they have been widely used to prepare varieties of POSS-based polymers and POSS-containing functional materials due to their unique characteristics of thermal stability, chemical stability, low dielectric properties and excellent biocompatibility. The study of POSS is an important integral part of nanocomposites. It has great significance in theory and application to select the new method for preparing the novel POSS monomers, developing the high performance POSS-based polymers and especially developing the POSS-containing polymers with special functionalities. In the present dissertation, two aspects had been focused. One was to prepare octaphenethyl POSS via the Friedel-Crafts alkylation reaction and use it to develop the novel POSS-based polymers. The other was to synthsize a series of POSS-based functional materials and particularly preparing the porous POSS-containing polymers through the Friedel-Crafts alkylation reaction.
1. The octaphenethyl POSS was prepared via Friedel-Crafts reaction by using octavinyl POSS and benzene as the starting materials. The POSS-based nanocomposites were prepared by solution blending of novolac resin and octaphenethyl POSS. FT-IR, POM, XRD and DSC were used to characterize the specific hydrogen bonding interaction, morphology and miscibility of phenolicresin/POSS nanocomposites before curing. The results indicated that there existed intermolecular hydrogen bonding interactions between the hydroxyl groups of the phenolic resin and Si-O-Si groups of POSS, which could promote POSS to disperse well in the polymer matrix up to20wt%POSS loading. At higher POSS loading, POSS would aggregate and lead to macrophase separation. Finally, the hexamethylene tetramine was used to cure the phenolic resin/POSS nanocomposites to form the network structure. The miscibility was also characterized by FT-IR and SEM. The results showed that the curing process prompted phase separation between the phenolic resin and POSS particles. DMA and TGA were also used to perform the thermal stability and mechanical properties of the cured phenolic resin/POSS nanocomposites.
2. A series of hybrid porous polymers (HPPs) were prepared via Friedel-Crafts reaction by using octavinyl POSS and benzene as the starting materials. The structures of hybrid porous polymers were characterized by FT-IR,13C CP/MAS NMR and29Si CP/MAS NMR. The porosities of hybrid porous polymers were determined by the N2sorption-desorption isotherms. The results showed that hybrid porous polymers featured both micro-and mesopores with apparent Brunauer-Emmett-Teller surface areas in a range of400～904m2g-1, with total pore volumes in the range of0.24cm3g-1to0.99cm3g-1. Their porosities can be fine tuned by adjusting the mole ratios of octavinyl POSS and benzene. The XRD, FE-SEM, HRTEM and TGA were also used to perform the morphologies and thermal stabilities of the hybrid porous polymers. The results showed that these polymers were amorphous porous polymers with high thermal stabilities. H2and CO2gas sorption isotherms were used to perform the sorption properties of the porous hybrid polymers. The results showed that the hybrids had preferable sorption properties and could be potentially applied to H2and CO2gas sorption. Finally, the hybrid porous polymers were postfunctionalized via the Thiol-ene Click reaction. The structures and properties of the postfunctionalised hybrid porous polymers were also characterized.
3. Eight kinds of the hybrid porous polymers were constructed by using octavinyl POSS and the non-planar molecules of biphenyl and1,3,5-triphenylbenzene via Friedel-Crafts alkylation, respectively. The structures of hybrid porous polymers were characterized by FT-IR,13C CP/MAS NMR and29Si CP/MAS NMR. And the porosities of hybrid porous polymers were tested by the N2sorption-desorption isotherms. The results showed that all hybrid porous polymers HPP-2, HPP-3, HPP-4, HPP-6, HPP-7and HPP-8, featured both micro-and mesopores with apparent Brunauer-Emmett-Teller surface areas in a range of600m2g-1to905m2g-1. The total pore volumes were in the range of0.51cm3g-1to0.55cm3g-1and0.55cm3g-1to0.76cm3g-1, respectively. As far as the hybrid porous polymers synthesized with the same building units, the total pore volumes of the hybrid porous polymers were similar, although the SBET of the hybrid porous polymers can be tuned by adjusting mole ratios of octavinyl POSS and non-planar molecules. The XRD, TGA, FE-SEM, HRTEM were also used to perform the thermal stabities and the morphologies of the hybrid porous polymers. The results show that hybrid porous polymers were featured micro-and mesopores, amorphous polmers with high thermal stability. Gas sorption isotherms were also used to characterize the performaces of the H2and CO2sorption properties of the hybrid porous polymers.
4. A variety of hyper-crosslinking polystyrene hybrids were prepared by using octavinyl POSS and polystyrene as building blocks via the Friedel-Crafts alkylation reaction. The structures of polystyrene hybrids porous polymers were characterized by FT-IR,13C CP/MAS NMR and29Si CP/MAS NMR. And the porosities of polystyrene hybrids were investigated by the N2sorption-desorption isotherms. The results show that hybrid porous polymers HPP-1, HPP-2, HPP-6and HPP-7featured both micro-and mesopores with SBET in a range of473m2g-1to767m2g-1, with total pore volumes in the range of0.36cm3g-1to0.90cm3g-1. The TGA, FE-SEM, HRTEM were also used to analyze the thermal stabities and the morphologies of the hybrid porous polymers. The results showed that hybrid porous polymers were amorphous polymers featured micro-and mesopores. Gas sorption isotherms were also used to characterize the performaces of the H2and CO2sorption properties of the hybrid porous polymers.
引文
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